TWI335324B - - Google Patents
Download PDFInfo
- Publication number
- TWI335324B TWI335324B TW092122022A TW92122022A TWI335324B TW I335324 B TWI335324 B TW I335324B TW 092122022 A TW092122022 A TW 092122022A TW 92122022 A TW92122022 A TW 92122022A TW I335324 B TWI335324 B TW I335324B
- Authority
- TW
- Taiwan
- Prior art keywords
- formula
- dimethyl
- compound
- producing
- type
- Prior art date
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/58—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4
- C07D311/70—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4 with two hydrocarbon radicals attached in position 2 and elements other than carbon and hydrogen in position 6
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/58—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Hydrogenated Pyridines (AREA)
Description
(9) (9)1335324 ’ 6.68 ( 1H，d，J = 7.8Hz ) ，6.99 ( ，d，J = 8. 1 Hz )， 7.01 ( 1 H > s ) 5 7.54 ( 1H > br)。 實施例3〜20 以式（3 )所示化合物（〇 · 5 g )作爲原料，變化金屬 催化劑的種類及使用量，腓的種類及使用量，溶劑的種類 及使用量，溫度，反應時間等時之原料（3 )，生成物（4 )及副產物（5 )的比率以HPLC相對面積百分比表示之 〇 又，金屬催化劑的種類，肼的種類，溶劑的種類，如 以卞記號所示。 又，金屬催化劑之使用量，以相對於原料使用量之質 4 %表示（含水物爲具含水量者），阱之使用量以相對於 原料之莫耳當量表示之，溶劑之使用量以相對於原料之質 曩倍表示之。 A : 5 % P d — C ( 5 0 % 含水物） B : 2%Pt — C ( 50%含水物）
C : 3%Pt - S 碳粉末（65 %含水物）（ENUIKEMCAT 公旬製） 肼的種類 D :肼水合物（80%者） E :肼水合物（98%者） 溶劑的種類 F :乙醇 -12- (10) 1335324 G :乙醇 /1，4 _ 二噁烷= 3/1 ( νΛ') Η:乙醇 / 水= 5/1 (v/v) I :異丙醇 J:乙醇 /1，4一 二噁烷=1/1 ( v/v ) K:乙醇 /1，4 —二噁烷=1/3 (v/v) 又，實施例4係於4 °C反應3小時後，以2 3 °C反應3 小時後各自之比率以HP LC相對面積百分比表示。
又，副產物（5 )之構造如以下所示
結果如表1所不。 -13- (11)1335324 表1 實施例 No. 催化劑 種類 量 肼 種類 量 溶劑 種類量 溫度 ro 時間 (hr) (3) 比率(％) (4) (5) 3 A 10 D 2.0 F 12 20-23 12 2.1 94.7 3.0 4 A 10 D 2.0 F 12 4 3 87.3 3.7 0.2 23 3 2.5 94.6 2.3 5 B 10 D 2.0 G 12 20 12 4.9 92.5 1.7 6 B 10 D 2.4 F 12 50-55 20 6.7 92.8 0.1 7 B 10 D 2.9 F 12 50-55 3 — 98.9 0.6 8 B 7.5 D 2.4 F 9 50-55 3 — 99.3 0.2 9 B 5 D 2.4 F 6 50-55 6 — 99.1 0.2 10 B 4 D 2.4 F 4 50-55 3 — 99.0 0.4 11 B 6 D 2.4 H 6 50-55 6 1.5 96.9 0.3 12 B 6 D 2.4 I 6 50-55 6 — 99.2 0.6 13 B 6 D 2.4 G 6 50-55 6 0.3 99.1 0.1 14 B 6 D 2.4 J 6 50-55 6 — 99.1 0.5 15 B 6 D 2.4 K 6 50-55 6 — 99.4 0.2 16 B 6 D 2.4 F 6 40-45 6 — 99.4 0.1 17 B 6 D 2.4 G 6 40-45 6 — 99.4 0.1 18 B 6 D 2.4 G 6 35-40 9 — 99.3 0.1 19 B 6 E 2.4 G 6 40-45 6 — 99.5 0.2 20 C 10 D 3.8 F 12 50-55 9 — 99.0 0.5
-14- (13) 1335324 又，表中之記號及單位與表1相同。 又，氫元素來源之種類如下述記號所示 氫元素來源之種類 L :氫氣（常壓：H2氣球） Μ ;甲酸銨 結果表2所不。 -16- (14)1335324 表2 比較例 催化劑 氫元素來源 溶劑 溫度時間 比率(％) No. 種類 量 種類 量 種類 量 (°C) (hr) (3) (4) ⑶ 2 A ]〇 L F 12 15-20 12 * - 91.9 3 A 10 M 4.0 F 12 15-20 12 - - 98.7 4 A 10 M 1.2 F 12 15-20 12 83.9 12.7 3.2 5 C 10 L F 12 15-20 4 8.1 63.6 20.4 6 C 10 L F 12 15-20 8 0.42 29.5 61.3 7 c 10 L F 12 15-20 30 . 91.9
-17 -
Claims (1)
1335324 p年 >月/日修(更 拾、申請專利範圍^ 一—~~~—I 第921 22022號專利申請案 中文申請專利範圍修正本 民國98年3月20日修正 1· 一種胺基苯并哌喃之製造方法，其特徵爲如式（1
(1)
所示之2,2—二甲基2H—1—苯并哌喃化合物之硝基 於鈀或鉑催化劑之存在下，以肼還元製造如式（2) H2N_C〇< (2) 所示之胺基苯并哌喃化合物。 2·如申請專利範圍第1項之胺基苯并哌喃之製造方 法’其中式（1)所示之2，2 —二甲基2H— 1—苯并哌喃 化合物爲式（3 ) 02N
(3)
所示之2，2 —二甲基6 —硝基2H— 1—苯并哌喃，式 (2)所示之胺基苯并哌喃化合物爲式（4) H2N
(4) 所示之6 —胺基2, 2_二甲基2H-1苯幷哌畴。 3.如申請專利範圍第1項或第2項之胺基苯并呢喃之 製造方法’其中上述肼之使用量，相對於丨莫耳當量22_ 1335324 二甲基2H— 1_苯并哌喃化合物爲2〜5莫耳當量。
-2-
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2002250112 | 2002-08-29 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| TW200407318A TW200407318A (en) | 2004-05-16 |
| TWI335324B true TWI335324B (zh) | 2011-01-01 |
Family
ID=31972610
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW092122022A TW200407318A (en) | 2002-08-29 | 2003-08-11 | Process for producing aminobenzopyran compound |
Country Status (22)
| Country | Link |
|---|---|
| US (1) | US7683189B2 (zh) |
| EP (1) | EP1535918B1 (zh) |
| JP (1) | JP4569755B2 (zh) |
| KR (1) | KR101078357B1 (zh) |
| CN (1) | CN100363358C (zh) |
| AT (1) | ATE486861T1 (zh) |
| AU (1) | AU2003252414B2 (zh) |
| CA (1) | CA2496847C (zh) |
| DE (1) | DE60334808D1 (zh) |
| DK (1) | DK1535918T3 (zh) |
| ES (1) | ES2353383T3 (zh) |
| HK (1) | HK1078874A1 (zh) |
| IL (1) | IL166886A (zh) |
| NO (1) | NO330794B1 (zh) |
| NZ (1) | NZ538745A (zh) |
| PT (1) | PT1535918E (zh) |
| RU (1) | RU2314302C2 (zh) |
| SI (1) | SI1535918T1 (zh) |
| TW (1) | TW200407318A (zh) |
| UA (1) | UA86000C2 (zh) |
| WO (1) | WO2004020428A1 (zh) |
| ZA (1) | ZA200501510B (zh) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20160168161A1 (en) | 2013-07-25 | 2016-06-16 | Nissan Chemical Industies, Ltd. | Method for producing heterocyclic compound |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1121307A (en) | 1964-08-07 | 1968-07-24 | Wellcome Found | New chromans and chromenes |
| CH624395A5 (zh) | 1976-01-08 | 1981-07-31 | Ciba Geigy Ag | |
| US5164509A (en) * | 1990-11-26 | 1992-11-17 | E. R. Squibb & Sons, Inc. | Benzodiazolo analogs |
| JPH0578289A (ja) * | 1991-09-18 | 1993-03-30 | Mitsui Toatsu Chem Inc | ２，７−ビス（４−アミノフエノキシ）ナフタレンおよびその製造方法 |
| JP2896268B2 (ja) * | 1992-05-22 | 1999-05-31 | 三菱電機株式会社 | 半導体基板の表面処理装置及びその制御方法 |
| KR100766676B1 (ko) | 1999-09-17 | 2007-10-15 | 닛산 가가쿠 고교 가부시키 가이샤 | 벤조피란 유도체 |
| JP2001151767A (ja) | 1999-09-17 | 2001-06-05 | Nissan Chem Ind Ltd | ベンゾピラン誘導体 |
| DE10023484A1 (de) * | 2000-05-09 | 2001-11-22 | Schering Ag | Anthranylamide und deren Verwendung als Arzneimittel |
-
2003
- 2003-08-06 WO PCT/JP2003/009987 patent/WO2004020428A1/ja active Application Filing
- 2003-08-06 PT PT03791193T patent/PT1535918E/pt unknown
- 2003-08-06 US US10/524,686 patent/US7683189B2/en not_active Expired - Fee Related
- 2003-08-06 JP JP2004532686A patent/JP4569755B2/ja not_active Expired - Fee Related
- 2003-08-06 SI SI200331910T patent/SI1535918T1/sl unknown
- 2003-08-06 ZA ZA200501510A patent/ZA200501510B/xx unknown
- 2003-08-06 UA UAA200502758A patent/UA86000C2/ru unknown
- 2003-08-06 CA CA2496847A patent/CA2496847C/en not_active Expired - Fee Related
- 2003-08-06 KR KR1020057003161A patent/KR101078357B1/ko not_active IP Right Cessation
- 2003-08-06 ES ES03791193T patent/ES2353383T3/es not_active Expired - Lifetime
- 2003-08-06 NZ NZ538745A patent/NZ538745A/en not_active IP Right Cessation
- 2003-08-06 RU RU2005108665/04A patent/RU2314302C2/ru not_active IP Right Cessation
- 2003-08-06 AT AT03791193T patent/ATE486861T1/de active
- 2003-08-06 AU AU2003252414A patent/AU2003252414B2/en not_active Ceased
- 2003-08-06 DE DE60334808T patent/DE60334808D1/de not_active Expired - Lifetime
- 2003-08-06 CN CNB038200821A patent/CN100363358C/zh not_active Expired - Fee Related
- 2003-08-06 EP EP03791193A patent/EP1535918B1/en not_active Expired - Lifetime
- 2003-08-06 DK DK03791193.0T patent/DK1535918T3/da active
- 2003-08-11 TW TW092122022A patent/TW200407318A/zh not_active IP Right Cessation
-
2005
- 2005-02-14 IL IL166886A patent/IL166886A/en not_active IP Right Cessation
- 2005-03-23 NO NO20051556A patent/NO330794B1/no not_active IP Right Cessation
- 2005-12-01 HK HK05110983.3A patent/HK1078874A1/xx not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| EP1535918A1 (en) | 2005-06-01 |
| NO330794B1 (no) | 2011-07-18 |
| CA2496847C (en) | 2011-06-07 |
| JPWO2004020428A1 (ja) | 2005-12-15 |
| RU2005108665A (ru) | 2005-08-10 |
| CA2496847A1 (en) | 2004-03-11 |
| ATE486861T1 (de) | 2010-11-15 |
| DE60334808D1 (de) | 2010-12-16 |
| US20050192444A1 (en) | 2005-09-01 |
| EP1535918B1 (en) | 2010-11-03 |
| PT1535918E (pt) | 2010-12-28 |
| NZ538745A (en) | 2007-06-29 |
| NO20051556L (no) | 2005-03-23 |
| TW200407318A (en) | 2004-05-16 |
| CN100363358C (zh) | 2008-01-23 |
| HK1078874A1 (en) | 2006-03-24 |
| KR20050036980A (ko) | 2005-04-20 |
| US7683189B2 (en) | 2010-03-23 |
| EP1535918A4 (en) | 2007-04-18 |
| SI1535918T1 (sl) | 2011-01-31 |
| CN1678603A (zh) | 2005-10-05 |
| ZA200501510B (en) | 2006-10-25 |
| AU2003252414B2 (en) | 2009-08-27 |
| UA86000C2 (ru) | 2009-03-25 |
| DK1535918T3 (da) | 2011-01-10 |
| ES2353383T3 (es) | 2011-03-01 |
| WO2004020428A1 (ja) | 2004-03-11 |
| KR101078357B1 (ko) | 2011-10-31 |
| IL166886A (en) | 2008-08-07 |
| AU2003252414A1 (en) | 2004-03-19 |
| NO20051556D0 (no) | 2005-03-23 |
| RU2314302C2 (ru) | 2008-01-10 |
| JP4569755B2 (ja) | 2010-10-27 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| TWI239943B (en) | Process for the purification of aliphatic aminonitriles | |
| CA2493538C (en) | Preparation of secondary amines | |
| TWI335324B (zh) | ||
| EP2524909B1 (en) | Preparation method of 4-aminomethylbenzoic acid | |
| KR100659913B1 (ko) | 알콜의제조방법 | |
| JP6999112B2 (ja) | ２，５－ビス（アミノメチル）フラン二ハロゲン化水素塩及びその製造方法並びに２，５－ビス（アミノメチル）フランの製造方法 | |
| RU2010134416A (ru) | Способ получения нитрилов | |
| EA201000847A1 (ru) | Способ получения кондесационной смолы | |
| CN109776492B (zh) | 一种反应型高选择性检测肼的荧光探针及其制备方法与应用 | |
| CN101085745A (zh) | 一种l－茶氨酸的改进合成方法 | |
| JP5289783B2 (ja) | ２−（イソプロピルアミノ）エタノールの製造方法 | |
| JPH10130210A (ja) | ジアミンの製造方法 | |
| Hauser | The Preparation and Cyclization of Chloroethyl Carbazates. Some Clarifications1 | |
| JP4393190B2 (ja) | ５−（３−ピリジルメチレン）イミダゾリジン−２，４−ジオンの製造方法 | |
| CN104402860A (zh) | 甲磺酸伊马替尼中间体的制备方法 | |
| JP2024056494A (ja) | ジフェニル尿素類の製造方法 | |
| EP1140787B1 (en) | Crosslinkers based on dibenzalacetone derivatives | |
| JPS5892657A (ja) | ラクタムの製造方法 | |
| JPH1112238A (ja) | １−（β−ヒドロキシエチル）−２，５−ジアミノベンゼン又はその塩の製造法 | |
| DE10344283A1 (de) | Verfahren zur Regelung der Reaktoreintrittstemperatur bei der Methylaminherstellung | |
| CN1690046A (zh) | L－茶氨酸的改良合成方法 | |
| KR20180103613A (ko) | 지방족 고리식 디아민 화합물의 개선된 합성 방법 | |
| JPS5948464A (ja) | ２−アルキル−４−アミノ−５−アミノメチルピリミジンの製法 | |
| JP2009137905A (ja) | 第三級アミンの製造方法 | |
| JP2007210936A (ja) | 脂環式ジアミン化合物の製造方法 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM4A | Annulment or lapse of patent due to non-payment of fees |