1,3-Cyclohexanedione → 2-Amino-4-(3-chlorophenyl)-1,4,5,6,7,8-hexahydro-5-oxoquinoline-3-carboxylic acid ethyl ester

HRID 268065Notes

Reaction equation

HRID 268065 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=O.[C:10]1(=[O:17])[CH2:15][CH2:14][CH2:13][C:12](=O)[CH2:11]1.[CH2:18]([O:20][C:21](=[O:26])[CH2:22][C:23](=[NH:25])[NH2:24])[CH3:19].C(O)C.CN(C=O)C>C(O)C>[CH2:18]([O:20][C:21]([C:22]1[CH:5]([C:4]2[CH:7]=[CH:8][CH:9]=[C:2]([Cl:1])[CH:3]=2)[C:11]2[C:10](=[O:17])[CH2:15][CH2:14][CH2:13][C:12]=2[NH:24][C:23]=1[NH2:25])=[O:26])[CH3:19]

Participants

6

Reactant 4

HCID 104341,3-CyclohexanedioneHCID 114773-ChlorobenzaldehydeHCID 4599837Carbamimidoyl-acetic acid ethyl esterHCID 19794673N,N-dimethylformamide ethanol

Product 1

HCID 123911082-Amino-4-(3-chlorophenyl)-1,4,5,6,7,8-hexahydro-5-oxoquinoline-3-carboxylic acid ethyl esterYield 66%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Upon boiling a solution of 7.1 g of 3-chlorobenzaldehyde, 5.6 g of cyclohexane-1,3-dione and 6.5 g of amidinoacetic acid ethyl ester in 150 ml of ethanol for 2 hours, 2-amino-4-(3-chlorophenyl)-1,4,5,6,7,8-hexahydro-5-oxoquinoline-3-carboxylic acid ethyl ester of melting point 266°C (ethanol/DMF) is obtained.

Workup

  1. customfor 2 hours

Sources & evidence

ORD record
ord-4002a9bef1584f7280929386827b3132
Source dataset
uspto-grants-1976_03
Patent number
US03946026

Reaction notes

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