GB611518A - Manufacture of quinacrine - Google Patents

Manufacture of quinacrine

Info

Publication number
GB611518A
GB611518A GB3126945A GB3126945A GB611518A GB 611518 A GB611518 A GB 611518A GB 3126945 A GB3126945 A GB 3126945A GB 3126945 A GB3126945 A GB 3126945A GB 611518 A GB611518 A GB 611518A
Authority
GB
United Kingdom
Prior art keywords
methoxy
diethylamino
specific gravity
acridine
dichloroacridine
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired
Application number
GB3126945A
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Eli Lilly and Co
Original Assignee
Eli Lilly and Co
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Eli Lilly and Co filed Critical Eli Lilly and Co
Priority to GB3126945A priority Critical patent/GB611518A/en
Publication of GB611518A publication Critical patent/GB611518A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D219/00—Heterocyclic compounds containing acridine or hydrogenated acridine ring systems
    • C07D219/04—Heterocyclic compounds containing acridine or hydrogenated acridine ring systems with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the ring system
    • C07D219/08—Nitrogen atoms
    • C07D219/10—Nitrogen atoms attached in position 9
    • C07D219/12—Amino-alkylamino radicals attached in position 9

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Materials For Photolithography (AREA)
  • Pyridine Compounds (AREA)
  • Catalysts (AREA)

Abstract

2-Methoxy - 6 - chloro - 9 -[11 - diethylamino-41-pentylamino]-acridine is prepared by reacting 2-methoxy-6 : 9-dichloroacridine and 1-diethylamino-4-aminopentane in the presence of at least one equivalent of phenol relative to the amount of 2-methoxy-6 : 9-dichloroacridine used, e.g. a 30 or 50 per cent excess may be employed, and treating the reaction mixture with sodium hydroxide and water in amounts sufficient to produce an aqueous alkaline layer having a specific gravity outside the range 1.062 to 1.130 and a layer containing the required substituted acridine. A specific gravity of less than 1.062 is preferred, for example, below 1.050 or 1.040. The layer containing the 2 - methoxy - 6 - chloro - 9 -[11 - diethylamino-41-pentylamino] acridine may be separated and washed with water. In an example, the specific gravity of the aqueous alkaline layer is 1.042 at 40 DEG C.ALSO:2 - Methoxy - 6 - chloro - 9 -[11 - diethylamino-41-pentylamino]-acridine is prepared by reacting 2-methoxy-6 : 9-dichloroacridine and 1-diethylamino-4-aminopentone in the presence of at least one equivalent of phenol relative to the amount of 2-methoxy-6 : 9-dichloroacridine used, e.g. a 30 or 50 per cent excess may be employed, and treating the reaction mixture with sodium hydroxide and water in amounts sufficient to produce an aqueous alkaline layer having a specific gravity outside the range 1.062 to 1.130 and a layer containing the required substituted acridine. A specific gravity of less than 1.062 is preferred, for example, below 1.050 or 1.040. The layer containing the 2-methoxy-6-chloro-9-[11-diethylamino-41-pentylamino] -acridine may be separated and washed with water. In an example, the specific gravity of the aqueous alkaline layer is 1.042 at 40 DEG C.
GB3126945A 1945-11-20 1945-11-20 Manufacture of quinacrine Expired GB611518A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB3126945A GB611518A (en) 1945-11-20 1945-11-20 Manufacture of quinacrine

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB3126945A GB611518A (en) 1945-11-20 1945-11-20 Manufacture of quinacrine

Publications (1)

Publication Number Publication Date
GB611518A true GB611518A (en) 1948-11-01

Family

ID=10320588

Family Applications (1)

Application Number Title Priority Date Filing Date
GB3126945A Expired GB611518A (en) 1945-11-20 1945-11-20 Manufacture of quinacrine

Country Status (1)

Country Link
GB (1) GB611518A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2003090665A2 (en) * 2002-04-26 2003-11-06 Florian Lang Regulation of erythrocyte apoptosis

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2003090665A2 (en) * 2002-04-26 2003-11-06 Florian Lang Regulation of erythrocyte apoptosis
WO2003090665A3 (en) * 2002-04-26 2004-01-08 Florian Lang Regulation of erythrocyte apoptosis

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