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

HRID 25774Notes

Reaction equation

HRID 25774 reaction equation
COC1C=CC=CC=1[C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[NH:15]C(C)(C)C=C2CSC(=O)C.Br[CH2:27][C:28]1[C:37]2[C:32](=[CH:33][CH:34]=[C:35]([C:38]3[CH:43]=[CH:42][CH:41]=[CH:40][C:39]=3[O:44][CH3:45])[CH:36]=2)[NH:31][C:30]([CH3:47])([CH3:46])[CH:29]=1.C(O)(=S)C.C(N(CC)CC)C>C(Cl)Cl>[CH3:45][O:44][C:39]1[CH:40]=[CH:41][CH:42]=[CH:43][C:38]=1[C:35]1[CH:36]=[C:37]2[C:32](=[CH:33][CH:34]=1)[NH:31][C:30]([CH3:47])([CH3:46])[CH:29]=[C:28]2[CH2:27][NH:15][C:16]1[CH:17]=[CH:18][CH:9]=[CH:10][CH:11]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 9998207Thioacetic acid S-[6-(2-methoxyphenyl)-2,2-dimethyl-1,2-dihydroquinolin-4-ylmethyl] esterHCID 225665354-(Bromomethyl)-6-(2-methoxyphenyl)-2,2-dimethyl-1,2-dihydroquinolineHCID 178418634HCID 178418634, compound

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Thioacetic acid S-[6-(2-methoxyphenyl)-2,2-dimethyl-1,2-dihydroquinolin-4-ylmethyl] ester 776 mg of 4-bromomethyl-6-(2-methoxyphenyl)-2,2-dimethyl-1,2-dihydroquinoline in 16 mL of methylene chloride was treated with 155 μL of thioacetic acid and 303 μL of triethylamine to give 100 mg of the title compound as a foam.

Sources & evidence

ORD record
ord-9ed43edf77e04ccc9d4905866af16f7a
Source dataset
uspto-grants-2005_02
Patent number
US06858627B2

Reaction notes

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