Carbamic acid, ethyl ester → 2-(Trifluoromethyl)-4-(3-cyanophenyl)-5-oxo-1,4,5,6,7,8-hexahydroquinoline-3-carboxylic acid
Reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH:9]2[C:18]3[C:17](=[O:19])[CH2:16][CH2:15][CH2:14][C:13]=3[NH:12][C:11]([C:20]([F:23])([F:22])[F:21])=[C:10]2[C:24]([O-:26])=[O:25])[CH:6]=[CH:7][CH:8]=1)#[N:2].NC(OCC)=O>>[C:1]([C:3]1[CH:4]=[C:5]([CH:9]2[C:18]3[C:17](=[O:19])[CH2:16][CH2:15][CH2:14][C:13]=3[NH:12][C:11]([C:20]([F:22])([F:23])[F:21])=[C:10]2[C:24]([OH:26])=[O:25])[CH:6]=[CH:7][CH:8]=1)#[N:2]Participants
3
Procedure
In the invented process, an ester of 4,4,4-trifluoro-3-oxobutanoate is reacted with 1,3-cyclohexanedione and 3-cyanobenzaldehyde to form an ester of 4-(3-cyanophenyl)-2-hydroxy-5-oxo-2-(trifluoromethyl)-1,2,3,4,5,6,7,8-octahydroquinoline-3-carboxylate. The 4-(3-cyanophenyl)-2-hydroxy-5-oxo-2-(trifluoromethyl)-1,2,3,4,5,6,7,8-octahydroquinoline-3-carboxylate ester is dehydrated to form a urethane, which is an ester of 4-(3-cyanophenyl)-5-oxo-2-(trifluoromethyl)-1,4,5,6,7,8-hexahydroquinoline-3-carboxylate. The urethane is de-esterified to form 4-(3-cyanophenyl)-5-oxo-2-(trifluoromethyl)-1,4,5,6,7,8-hexahydroquinoline-3-carboxylic acid.
Sources & evidence
- ORD record
- ord-c9e68479fd22490e96e1882ea71b15ce
- Source dataset
- uspto-grants-2006_03
- Patent number
- US07012145B2
Reaction notes
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