4-(3-Chloro-2-methoxyphenyl)-2-hydroxy-4-methyl-2-(trifluoromethyl)pentanal → 5-{[6-Chloro-4,4-dimethyl-2-hydroxy-5-methoxy-2-(trifluoromethyl)-1,2,3,4-tetrahydronaphthalen-1-yl]amino}-8-fluoro-quinolin-2(1H)-one

HRID 1869441Notes

Reaction equation

HRID 1869441 reaction equation
[Cl:1][C:2]1[C:3]([O:20][CH3:21])=[C:4]([C:8]([CH3:19])([CH3:18])[CH2:9][C:10]([OH:17])([C:13]([F:16])([F:15])[F:14])[CH:11]=O)[CH:5]=[CH:6][CH:7]=1.[NH2:22][C:23]1[CH:32]=[CH:31][C:30]([F:33])=[C:29]2[C:24]=1[CH:25]=[CH:26][C:27](=[O:34])[NH:28]2>>[Cl:1][C:2]1[C:3]([O:20][CH3:21])=[C:4]2[C:5](=[CH:6][CH:7]=1)[CH:11]([NH:22][C:23]1[CH:32]=[CH:31][C:30]([F:33])=[C:29]3[C:24]=1[CH:25]=[CH:26][C:27](=[O:34])[NH:28]3)[C:10]([OH:17])([C:13]([F:16])([F:15])[F:14])[CH2:9][C:8]2([CH3:19])[CH3:18]

Participants

3

Reactant 2

HCID 179891374-(3-Chloro-2-methoxyphenyl)-2-hydroxy-4-methyl-2-(trifluoromethyl)pentanalHCID 179891895-amino-8-fluoroquinolin-2(1H)-one

Product 1

HCID 686817075-{[6-Chloro-4,4-dimethyl-2-hydroxy-5-methoxy-2-(trifluoromethyl)-1,2,3,4-tetrahydronaphthalen-1-yl]amino}-8-fluoro-quinolin-2(1H)-one

Procedure

Analogously to Example 10, the corresponding imine is produced starting from 250 g of 4-(3-chloro-2-methoxyphenyl)-2-hydroxy-4-methyl-2-(trifluoromethyl)pentanal and 137 mg of 5-amino-8-fluoroquinolin-2(1H)-one. The title compound is obtained analogously to Example 3 by reaction of the imine that is formed with 1.4 ml of titanium tetrachloride solution (1 M in dichloromethane).

Sources & evidence

ORD record
ord-df57e59902e74b118fe7506e228a0dba
Source dataset
uspto-grants-2009_12
Patent number
US07638515B2

Reaction notes

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