Ethanol → 1,3-Cyclohexanedione

HRID 918502Notes

Reaction equation

HRID 918502 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH:15]([C:16]2[CH:21]=[CH:20][C:19]([N+:22]([O-:24])=[O:23])=[CH:18][C:17]=2[C:25]([F:28])([F:27])[F:26])[C:14]2[C:13](=[O:29])[CH2:12][CH2:11][CH2:10][C:9]=2[NH:8][C:7]=1[NH2:30])=[O:5])[CH3:2].C([OH:33])C>>[F:26][C:25]([F:28])([F:27])[C:17]1[CH:18]=[C:19]([N+:22]([O-:24])=[O:23])[CH:20]=[CH:21][C:16]=1[CH:15]=[O:33].[C:13]1(=[O:29])[CH2:12][CH2:11][CH2:10][C:9](=[O:33])[CH2:14]1.[CH2:1]([O:3][C:4](=[O:5])[CH2:6][C:7](=[NH:8])[NH2:30])[CH3:2]

Participants

5

Reactant 2

HCID 702Ethanol2×HCID 123911132-Amino-4-(2-trifluoromethyl-4-nitrophenyl)-1,4,5,6,7,8-hexahydro-5-oxoquinoline-3-carboxylic acid ethyl ester

Product 3

HCID 104341,3-CyclohexanedioneHCID 4599837Carbamimidoyl-acetic acid ethyl esterHCID 123911054-Nitro-2-(trifluoromethyl)benzaldehyde

Procedure

Upon heating a solution of 11.0 g. of 2-trifluoromethyl-4-nitrobenzaldehyde, 5.6 g of cyclohexane-1,3-dione and 6.5 g of amidinoacetic acid ethyl ester in 250 ml of ethanol of 2 hours, 2-amino-4-(2-trifluoromethyl-4-nitrophenyl)-1,4,5,6,7,8-hexahydro-5-oxoquinoline-3-carboxylic acid ethyl ester of melting point 264°C (ethanol) is obtained. Yield: 62% of theory.

Workup

  1. temperatureUpon heating a solution of 11.0 g

Sources & evidence

ORD record
ord-0408c0e5fa26414780825dd1a44f3ad9
Source dataset
uspto-grants-1976_07
Patent number
US03971791

Reaction notes

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