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

HRID 25770

Reaction equation

[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[NH:15][C:14]([CH3:20])([CH3:19])[CH:13]=[C:12]2[CH2:21]SC1C=CC2C(=CC=CC=2)C=1.BrCC1[C:44]2[C:39](=[CH:40][CH:41]=[C:42](C3C=CC=CC=3OC)[CH:43]=2)[NH:38]C(C)(C)C=1.C(=O)([O-])[O-].[K+].[K+].C1C2C(=CC=CC=2)C=CC=1S>>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[NH:15][C:14]([CH3:20])([CH3:19])[CH:13]=[C:12]2[CH2:21][NH:38][C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1

Participants

Reactant 4

HCID 70582-Naphthalenethiol

HCID 11430Potassium Carbonate

HCID 100032256-(2-Methoxyphenyl)-2,2-dimethyl-4-(naphthalen-2-ylsulfanylmethyl)-1,2-dihydroquinoline

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]phenylamine

Procedure

6-(2-Methoxyphenyl)-2,2-dimethyl-4-(naphthalen-2-ylsulfanylmethyl)-1,2-dihydroquinoline 100 mg of 4-bromomethyl-6-(2-methoxyphenyl)-2,2-dimethyl-1,2-dihydroquinoline, 80 mg of potassium carbonate, and 42 mg of 2-naphthalenethiol reacted to give 8 mg of the title compound as an oil.

Sources & evidence

ORD record: ord-cbfc5c9e672e4166b815af582066c4ec
Source dataset: uspto-grants-2005_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06858627B2

Linked notes

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