Potassium Carbonate → [6-(2-Methoxyphenyl)-2,2-dimethyl-1,2-dihydroquinolin-4-ylmethyl]phenylamine

HRID 25769Notes

Reaction equation

HRID 25769 reaction equation
COC(=O)CSCC1[C:16]2[C:11](=[CH:12][CH:13]=[C:14](C3C=CC=CC=3OC)[CH:15]=2)[NH:10]C(C)(C)C=1.Br[CH2:29][C:30]1[C:39]2[C:34](=[CH:35][CH:36]=[C:37]([C:40]3[CH:45]=[CH:44][CH:43]=[CH:42][C:41]=3[O:46][CH3:47])[CH:38]=2)[NH:33][C:32]([CH3:49])([CH3:48])[CH:31]=1.C(=O)([O-])[O-].[K+].[K+].C(OC)(=O)CS>>[CH3:47][O:46][C:41]1[CH:42]=[CH:43][CH:44]=[CH:45][C:40]=1[C:37]1[CH:38]=[C:39]2[C:34](=[CH:35][CH:36]=1)[NH:33][C:32]([CH3:49])([CH3:48])[CH:31]=[C:30]2[CH2:29][NH:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

5

Reactant 4

HCID 11430Potassium CarbonateHCID 16907Methyl ThioglycolateHCID 10091387[6-(2-Methoxyphenyl)-2,2-dimethyl-1,2-dihydroquinolin-4-ylmethylsulfanyl]acetic acid methyl esterHCID 225665354-(Bromomethyl)-6-(2-methoxyphenyl)-2,2-dimethyl-1,2-dihydroquinoline

Product 1

HCID 10406857[6-(2-Methoxyphenyl)-2,2-dimethyl-1,2-dihydroquinolin-4-ylmethyl]phenylamine

Procedure

[6-(2-Methoxyphenyl)-2,2-dimethyl-1,2-dihydroquinolin-4-ylmethylsulfanyl]acetic acid methyl ester 100 mg of 4-bromomethyl-6-(2-methoxyphenyl)-2,2-dimethyl-1,2-dihydroquinoline, 80 mg of potassium carbonate, and 52 μL of methyl thioglycolate reacted to give 4 mg of the title compound as an oil.

Sources & evidence

ORD record
ord-390ae158c3434d0cb417529d902c8813
Source dataset
uspto-grants-2005_02
Patent number
US06858627B2

Reaction notes

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