2-Naphthylamine → HCID 68681106, compound

HRID 1444500Notes

Reaction equation

HRID 1444500 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.[CH:21]1[C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[CH:24]=[CH:23][C:22]=1[NH2:31]>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:22]1[CH:23]=[CH:24][C:25]2[C:30](=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH:21]=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 70572-NaphthylamineHCID 17989098HCID 17989098, compound

Product 1

HCID 68681106HCID 68681106, compoundYield 89.8%

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 2-naphthylamine in toluene with the aid of titanium tetraisopropylate. After working-up and chromatography, 192.8 mg (89.8%) of the desired imine is isolated.

Sources & evidence

ORD record
ord-734750eb979e40a28d0f15b5437352d3
Source dataset
uspto-grants-2010_02
Patent number
US07662821B2

Reaction notes

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