2-Chlorobenzaldehyde → 4-(2-Chlorophenyl)-3-ethoxycarbonyl-6,6-dimethyl-2-[2-(2-methylbenzimidazol-1-yl)ethoxymethyl]-1,4,5,6,7,8-hexahydro-5-oxoquinoline

HRID 981522Notes

Reaction equation

[Cl:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=O.[NH2:10][C:11]1[CH2:16][CH2:15][C:14]([CH3:18])([CH3:17])[C:13](=[O:19])[CH:12]=1.[CH3:20][C:21]1[N:25]([CH2:26][CH2:27][O:28][CH2:29][C:30](=O)[CH2:31][C:32]([O:34][CH2:35][CH3:36])=[O:33])[C:24]2[CH:38]=[CH:39][CH:40]=[CH:41][C:23]=2[N:22]=1>>[Cl:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]1[C:12]2[C:13](=[O:19])[C:14]([CH3:18])([CH3:17])[CH2:15][CH2:16][C:11]=2[NH:10][C:30]([CH2:29][O:28][CH2:27][CH2:26][N:25]2[C:24]3[CH:38]=[CH:39][CH:40]=[CH:41][C:23]=3[N:22]=[C:21]2[CH3:20])=[C:31]1[C:32]([O:34][CH2:35][CH3:36])=[O:33]

Participants

Reactant 3

HCID 69962-Chlorobenzaldehyde

HCID 181871753-Amino-6,6-dimethylcyclohex-2-en-1-one

HCID 20070378Ethyl 4-[2-(2-methylbenzimidazol-1-yl)ethoxy]-3-oxobutanoate

Product 1

HCID 200703764-(2-Chlorophenyl)-3-ethoxycarbonyl-6,6-dimethyl-2-[2-(2-methylbenzimidazol-1-yl)ethoxymethyl]-1,4,5,6,7,8-hexahydro-5-oxoquinolineYield 11.5%

Procedure

The title compound (63 mg) was prepared from 2-chlorobenzaldehyde (202 mg), 3-amino-6,6-dimethyl-2-cyclohexene-1-one (200 mg) and ethyl 4-[2-(2-methylbenzimidazol-1-yl)ethoxy]-3-oxobutanoate (304 mg) by the method of Example 1. M.p. 118°-120° C.

Sources & evidence

ORD record: ord-f46ec38a5fb94fe99351ec4be23b207b
Source dataset: uspto-grants-1991_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04992447

Reaction notes

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