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

HRID 268064Notes

Reaction equation

HRID 268064 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][CH:11]=1)[CH:7]=O)([O-:3])=[O:2].[C:12]1(=[O:19])[CH2:17][CH2:16][CH2:15][C:14](=O)[CH2:13]1.[CH2:20]([O:22][C:23](=[O:28])[CH2:24][C:25](=[NH:27])[NH2:26])[CH3:21]>>[CH2:20]([O:22][C:23]([C:24]1[CH:7]([C:6]2[CH:9]=[CH:10][CH:11]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=2)[C:13]2[C:12](=[O:19])[CH2:17][CH2:16][CH2:15][C:14]=2[NH:26][C:25]=1[NH2:27])=[O:28])[CH3:21]

Participants

4

Reactant 3

HCID 74493-NitrobenzaldehydeHCID 104341,3-CyclohexanedioneHCID 4599837Carbamimidoyl-acetic acid ethyl ester

Product 1

HCID 123911172-Amino-4-(3-nitrophenyl)-1,4,5,6,7,8-hexahydro-5-oxoquinoline-3-carboxylic acid ethyl esterYield 61%

Procedure

Upon boiling a solution of 7.6 g of 3-nitrobenzaldehyde, 5.6 g of cyclohexane-1,3-dione and 6.5 g of amidinoacetic acid ethyl ester for 1 hour, 2-amino-4-(3-nitrophenyl)-1,4,5,6,7,8-hexahydro-5-oxoquinoline-3-carboxylic acid ethyl ester of melting point >260°C is obtained (alcohol/DMF).

Workup

  1. customfor 1 hour

Sources & evidence

ORD record
ord-556dbc3536db49deb7722411c358dd5e
Source dataset
uspto-grants-1976_03
Patent number
US03946026

Reaction notes

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