1-Naphthylamine → HCID 68679045, compound

HRID 1869415Notes

Reaction equation

HRID 1869415 reaction equation
[OH:1][C:2]([C:17]([F:20])([F:19])[F:18])([CH2:5][C:6]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[O:15][CH3:16])([CH3:8])[CH3:7])[CH:3]=O.[C:21]1([NH2:31])[C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[CH:24]=[CH:23][CH:22]=1>C1(C)C=CC=CC=1.CC([O-])C.CC([O-])C.CC([O-])C.CC([O-])C.[Ti+4]>[F:20][C:17]([F:18])([F:19])[C:2]([CH:3]=[N:31][C:21]1[C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[CH:24]=[CH:23][CH:22]=1)([OH:1])[CH2:5][C:6]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[O:15][CH3:16])([CH3:7])[CH3:8]

Participants

5

Reactant 2

HCID 86401-NaphthylamineHCID 179890984-(2-Methoxyphenyl)-2-hydroxy-4-methyl-2-(trifluoromethyl)pentanal

Product 1

HCID 68679045HCID 68679045, compoundYield 77.7%

Reagents, catalysts & solvents 2

HCID 11026Titanium isopropoxideCatalystHCID 1140TolueneSolvent

Procedure

150 mg (0.517 mmol) of 2-hydroxy-4-(2-methoxyphenyl)-4-methyl-2-(trifluoromethyl)-pentanal is converted into imine with 74 mg (0.517 mmol) of 1-naphthylamine in toluene with the aid of titanium tetraisopropylate. After working-up and chromatography, 166.7 mg (77.7%) of the desired imine is isolated.

Sources & evidence

ORD record
ord-26edccf0578841f18a61809b52f5e35c
Source dataset
uspto-grants-2009_12
Patent number
US07638515B2

Reaction notes

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