Diethyl Ether → 4-Amino-5-chloro-2-methoxy-N-(octahydro-2H-quinolizin-2-yl)benzamide

HRID 2057891Notes

Reaction equation

HRID 2057891 reaction equation
C([NH:4][C:5]1[C:23]([Cl:24])=[CH:22][C:8]([C:9]([NH:11][CH:12]2[CH2:21][CH2:20][N:19]3[CH:14]([CH2:15][CH2:16][CH2:17][CH2:18]3)[CH2:13]2)=[O:10])=[C:7]([O:25][CH3:26])[CH:6]=1)(=O)C.[OH-].[K+].CCOCC>C(O)C.O>[NH2:4][C:5]1[C:23]([Cl:24])=[CH:22][C:8]([C:9]([NH:11][CH:12]2[CH2:21][CH2:20][N:19]3[CH:14]([CH2:15][CH2:16][CH2:17][CH2:18]3)[CH2:13]2)=[O:10])=[C:7]([O:25][CH3:26])[CH:6]=1

Participants

6

Reactant 3

HCID 3283Diethyl EtherHCID 14797Potassium HydroxideHCID 12783918HCID 12783918, compound

Product 1

HCID 127839214-Amino-5-chloro-2-methoxy-N-(octahydro-2H-quinolizin-2-yl)benzamideYield 75%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

Hydrolysis of 4-acetylamino-5-chloro-2-methoxy-N-(2-quinolizidinyl)-benzamide (600 mg) with potassium hydroxide (500 mg) in ethanol (10 ml) and water (2 ml) at reflux for 4 hours followed by isolation through ether afforded one of the isomers of 4-amino-5-chloro-2-methoxy-N-(2-quinolizidinyl)-benzamide (400 mg), m.p. 175°-8°.

Workup

  1. temperatureat reflux for 4 hours

Sources & evidence

ORD record
ord-7056ebe655bc44d4bbf2e3bd96525d7c
Source dataset
uspto-grants-1980_07
Patent number
US04213983

Reaction notes

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