1,3-Cyclohexanedione → HCID 3701157, compound

HRID 268079Notes

Reaction equation

HRID 268079 reaction equation
[Br: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>[CH2:18]([O:20][C:21]([C:22]1[CH:5]([C:4]2[CH:7]=[CH:8][CH:9]=[C:2]([Br: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

5

Reactant 3

HCID 104341,3-CyclohexanedioneHCID 765833-BromobenzaldehydeHCID 4599837Carbamimidoyl-acetic acid ethyl ester

Product 1

HCID 3701157HCID 3701157, compoundYield 44%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

Upon heating a solution of 9.3 g of 3-bromobenzaldehyde, 5.6 g of cyclohexane-1,3-dione and 6.5 g of amidinoacetic acid ethyl ester in 100 ml of ethanol for 8 hours, 2-amino-4-(3-bromophenyl)-1,4,5,6,7,8-hexahydro-5-oxoquinoline-3-carboxylic acid ethyl ester of melting point 255°C (ethanol) is obtained.

Sources & evidence

ORD record
ord-3ee7b46b22ab476c97aa6f35177e217c
Source dataset
uspto-grants-1976_03
Patent number
US03946026

Reaction notes

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