Dichloromethane → 5-{[2-Hydroxy-5-methoxy-2-(trifluoromethyl)-4,4,6-trimethyl-1,2,3,4-tetrahydronaphthalen-1-yl]amino}-quinolin-2(1H)-one

HRID 1443252Notes

Reaction equation

HRID 1443252 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7](C)[CH:6]=[CH:5][C:4]=1[C:10]([CH3:21])([CH3:20])[CH2:11][C:12]([OH:19])([C:15]([F:18])([F:17])[F:16])[CH:13]=O.[NH2:22][C:23]1[CH:32]=[CH:31][CH:30]=[C:29]2[C:24]=1[CH:25]=[CH:26][C:27](=[O:33])[NH:28]2.Cl[CH2:35]Cl>[Ti](Cl)(Cl)(Cl)Cl>[OH:19][C:12]1([C:15]([F:16])([F:18])[F:17])[CH2:11][C:10]([CH3:20])([CH3:21])[C:4]2[C:5](=[CH:6][CH:7]=[C:8]([CH3:35])[C:3]=2[O:2][CH3:1])[CH:13]1[NH:22][C:23]1[CH:32]=[CH:31][CH:30]=[C:29]2[C:24]=1[CH:25]=[CH:26][C:27](=[O:33])[NH:28]2

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 157190785-Amino-1,2-dihydroquinolin-2-oneHCID 179891274-(2-Methoxy-4-methylphenyl)-2-hydroxy-4-methyl-2-(trifluoromethyl)pentanal

Product 1

HCID 686824875-{[2-Hydroxy-5-methoxy-2-(trifluoromethyl)-4,4,6-trimethyl-1,2,3,4-tetrahydronaphthalen-1-yl]amino}-quinolin-2(1H)-one

Reagents, catalysts & solvents 1

HCID 24193Titanium TetrachlorideCatalyst

Procedure

Analogously to Example 10, the corresponding imine is produced starting from 600 mg of 4-(2-methoxy-4-methylphenyl)-2-hydroxy-4-methyl-2-(trifluoromethyl)pentanal and 315 mg of 5-aminoquinolin-2(1H)-one. 12 mg of the title compound is obtained by reaction of 370 mg of the imine with 8.3 ml of titanium tetrachloride (1 M in dichloromethane) in 20 ml of dichloromethane.

Sources & evidence

ORD record
ord-0f228e19f28d488fa4316ebe48f322e9
Source dataset
uspto-grants-2010_02
Patent number
US07659297B2

Reaction notes

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