Aniline → 2-Phenylamino-6,7,8,9,9a,10-hexahydro-5aH-benzo[g]quinolin-5-one

HRID 1817831Notes

Reaction equation

HRID 1817831 reaction equation
Cl[CH:2]1[CH:11]=[CH:10][C:9]2[C:8](=[O:12])[CH:7]3[CH2:13][CH2:14][CH2:15][CH2:16][CH:6]3[CH2:5][C:4]=2[NH:3]1.[NH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=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>[C:18]1([NH:17][C:2]2[CH:11]=[CH:10][C:9]3[C:8](=[O:12])[CH:7]4[CH2:13][CH2:14][CH2:15][CH2:16][CH:6]4[CH2:5][C:4]=3[N:3]=2)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

6

Reactant 3

HCID 6115AnilineHCID 2733478Sodium 2-methylbutan-2-olateHCID 690381592-chloro-2,5a,6,7,8,9,9a,10-octahydro-1H-benzo[g]quinolin-5-one

Product 1

HCID 578832922-Phenylamino-6,7,8,9,9a,10-hexahydro-5aH-benzo[g]quinolin-5-oneYield 6%

Reagents, catalysts & solvents 2

HCID 178418851HCID 178418851, compoundCatalystHCID 1140TolueneSolvent

Procedure

To a solution of 2-chloro-2,5a,6,7,8,9,9a,10-octahydro-1H-benzo[g]quinolin-5-one (0.4 g, 1.7 mmol) and aniline (0.204 g, 2.2 mmol) in toluene (2 ml) under an argon atmosphere was added sodium tert-amylate (0.223 g, 2.2 mmol) and bis(tri-tert-butylphosphine)palladium (0.043 g, 0.085 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 (0.03 g, 6%) 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-33c42113b6c04842bcaf397c69f89987
Source dataset
uspto-grants-2009_10
Patent number
US07598384B2

Reaction notes

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