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

HRID 25760

Reaction equation

C(SCC1[C:15]2[C:10](=[CH:11][CH:12]=[C:13](C3C=CC=CC=3)[CH:14]=2)[NH:9]C(C)(C)C=1)C=C.Br[CH2:25][C:26]1[C:35]2[C:30](=[CH:31][CH:32]=[C:33]([C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][C:37]=3[O:42][CH3:43])[CH:34]=2)[NH:29][C:28]([CH3:45])([CH3:44])[CH:27]=1.C(=O)([O-])[O-].[K+].[K+].C(S)C=C>>[CH3:43][O:42][C:37]1[CH:38]=[CH:39][CH:40]=[CH:41][C:36]=1[C:33]1[CH:34]=[C:35]2[C:30](=[CH:31][CH:32]=1)[NH:29][C:28]([CH3:45])([CH3:44])[CH:27]=[C:26]2[CH2:25][NH:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

Reactant 4

HCID 11430Potassium Carbonate

HCID 13367Allyl Mercaptan

HCID 103362084-Allylsulfanylmethyl-2,2-dimethyl-6-phenyl-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

4-Allylsulfanylmethyl-2,2-dimethyl-6-phenyl-1,2-dihydroquinoline 40 mg of 4-bromomethyl-6-(2-methoxyphenyl)-2,2-dimethyl-1,2-dihydroquinoline, 46 mg of potassium carbonate, and 44 μL of allyl mercaptan reacted to give 5 mg of the title compound as an oil.

Sources & evidence

ORD record: ord-152309d9e4b24a4dbec8c8e16c163aa9
Source dataset: uspto-grants-2005_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06858627B2

Linked notes

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