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

HRID 25751

Reaction equation

Cl[C:2]1[CH:3]=[C:4]([NH:9][CH2:10][C:11]2[C:20]3[C:15](=[CH:16][CH:17]=[C:18]([C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=4[O:27][CH3:28])[CH:19]=3)[NH:14][C:13]([CH3:30])([CH3:29])[CH:12]=2)[CH:5]=[C:6](Cl)[CH:7]=1.BrCC1C2C(=CC=C(C3C=CC=CC=3OC)C=2)NC(C)(C)C=1.C(=O)([O-])[O-].[K+].[K+].ClC1C=C(C=C(Cl)C=1)N>>[CH3:28][O:27][C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=1[C:18]1[CH:19]=[C:20]2[C:15](=[CH:16][CH:17]=1)[NH:14][C:13]([CH3:30])([CH3:29])[CH:12]=[C:11]2[CH2:10][NH:9][C:4]1[CH:5]=[CH:6][CH:7]=[CH:2][CH:3]=1

Participants

Reactant 4

HCID 11430Potassium Carbonate

HCID 122813,5-Dichloroaniline

HCID 10071884(3,5-Dichlorophenyl)-[6-(2-methoxyphenyl)-2,2-dimethyl-1,2-dihydroquinolin-4-ylmethyl]amine

HCID 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]phenylamineYield 71.2%

Procedure

(3,5-Dichlorophenyl)-[6-(2-methoxyphenyl)-2,2-dimethyl-1,2-dihydroquinolin-4-ylmethyl]amine 2 mg of 4-bromomethyl-6-(2-methoxyphenyl)-2,2-dimethyl-1,2-dihydroquinoline, 32 mg of potassium carbonate, and 20 mg of 3,5-dichloroaniline reacted to give 1.2 mg of the title compound as a foam.

Sources & evidence

ORD record: ord-2262e2887f20488e98cfb04e440874f7
Source dataset: uspto-grants-2005_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06858627B2

Linked notes

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