P-Anisidine → 2-(4-Methoxy-phenylamino)-7,7-dimethyl-7,8-dihydro-6H-quinolin-5-one

HRID 1817825Notes

Reaction equation

HRID 1817825 reaction equation
Cl[C:2]1[CH:11]=[CH:10][C:9]2[C:8](=[O:12])[CH2:7][C:6]([CH3:14])([CH3:13])[CH2:5][C:4]=2[N:3]=1.[CH3:15][O:16][C:17]1[CH:22]=[CH:21][C:20]([NH2:23])=[CH:19][CH:18]=1.CCC([O-])(C)C.[Na+]>C1(C)C=CC=CC=1.CC(C)([P](C(C)(C)C)([Pd][P](C(C)(C)C)(C(C)(C)C)C(C)(C)C)C(C)(C)C)C>[CH3:15][O:16][C:17]1[CH:22]=[CH:21][C:20]([NH:23][C:2]2[CH:11]=[CH:10][C:9]3[C:8](=[O:12])[CH2:7][C:6]([CH3:14])([CH3:13])[CH2:5][C:4]=3[N:3]=2)=[CH:19][CH:18]=1

Participants

6

Reactant 3

HCID 7732P-AnisidineHCID 2733478Sodium 2-methylbutan-2-olateHCID 148125452-Chloro-7,7-dimethyl-7,8-dihydroquinolin-5(6H)-one

Product 1

HCID 578832692-(4-Methoxy-phenylamino)-7,7-dimethyl-7,8-dihydro-6H-quinolin-5-oneYield 19.4%

Reagents, catalysts & solvents 2

HCID 178418851HCID 178418851, compoundCatalystHCID 1140TolueneSolvent

Procedure

To a solution of 2-chloro-7,7-dimethyl-7,8-dihydro-6H-quinolin-5-one (0.35 g, 1.67 mmol) and 4-methoxyphenylamine (0.267 g, 2.2 mmol) in toluene (2 ml) under an argon atmosphere was added sodium tert-amylate (0.22 g, 2.0 mmol) and bis(tri-tert-butylphosphine)palladium (0.043 g, 0.084 mmol). The mixture was heated at reflux for 8 h. Then it was concentrated under reduced pressure and the residue was purified by column chromatography on silica gel to give the title compound (0.096 g, 19%) as a colorless solid.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 8 h
  3. concentrationThen it was concentrated under reduced pressure
  4. customthe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-bda95fe18370456c974de73b798ca083
Source dataset
uspto-grants-2009_10
Patent number
US07598384B2

Reaction notes

Loading…