Benzoyl chloride → HCID 54486858, compound

HRID 326099Notes

Reaction equation

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

Participants

Reactant 2

HCID 7412Benzoyl chloride

HCID 54148152HCID 54148152, compound

Product 1

HCID 54486858HCID 54486858, compound

Procedure

12,2 g of 1-phenyl-pyrimido[1,6-a]indole-5-acetic acid ethyl ester (m.p. 59°-62°), obtained from 2-aminoethyl-indole-3-acetic acid ethyl ester and benzoylchloride and the resulting 1-phenyl-3,4-dihydro-pyrimido[1,6-a]indole-5-acetic acid ethyl ester (m.p. 83°-84°), are stirred with 30 ml of ethanol and 40 ml of 2n sodium hydroxide in the course of 3 hours at room temperature. The mixture is acidified with concentrated hydrochloric acid to pH=3 and 30 ml of propyleneoxide, while stirring, are added. After short time 1-phenyl-pyrimido[1,6-a]indole-5-acetic acid crystallises out and is filtered off. The acid is recrystallised from ethanol, m.p. 198-204 (decomposition).

Sources & evidence

ORD record: ord-fd9e79859a884d21ac3e64e915ae0afe
Source dataset: uspto-grants-1984_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04444768

Reaction notes

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