HCID 67291102, compound → 2-(4,4-Dimethyl-6-(trifluoromethyl)-1,2,3,4-tetrahydroquinolin-2-yl)aniline

HRID 1036921Notes

Reaction equation

HRID 1036921 reaction equation
[CH3:1][C:2]1([CH3:25])[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([C:12]([F:15])([F:14])[F:13])[CH:10]=2)[NH:5][CH:4]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[N+:22]([O-])=O)[CH2:3]1>[Cl-].[NH4+].C(O)C.[Fe]>[CH3:1][C:2]1([CH3:25])[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([C:12]([F:14])([F:13])[F:15])[CH:10]=2)[NH:5][CH:4]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[NH2:22])[CH2:3]1

Participants

5

Reactant 1

HCID 67291102HCID 67291102, compound

Product 1

HCID 672899892-(4,4-Dimethyl-6-(trifluoromethyl)-1,2,3,4-tetrahydroquinolin-2-yl)aniline

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 702EthanolSolventHCID 25517Ammonium ChlorideSolvent

Procedure

To a suspension of 4,4-dimethyl-2-(2-nitrophenyl)-6-(trifluoromethyl)-1,2,3,4-tetrahydroquinoline (2.56 g, 7.3 mmol) in saturated aqueous ammonium chloride (20 mL) and ethanol (30 mL) was added iron powder (1.2 g, 21.0 mmol) at room temperature After addition, the resulting mixture was stirred at reflux under Nitrogen for 3 h. The reaction mixture was cooled to room temperature and filtered through a pad of celite. The solvent of ethanol in filtrate was removed under reduced pressure and the water phase was extracted with ethyl acetate. The combined organic phase was dried, concentrated to give 2-(4,4-dimethyl-6-(trifluoromethyl)-1,2,3,4-tetrahydroquinolin-2-yl)aniline. The product was used in the next step without further purification. LC/MS m/e obsd. (ESI+) [(M+H)+] 321.1.

Workup

  1. additionAfter addition
  2. temperatureat reflux under Nitrogen for 3 h
  3. filtrationfiltered through a pad of celite
  4. customThe solvent of ethanol in filtrate was removed under reduced pressure
  5. extractionthe water phase was extracted with ethyl acetate
  6. customThe combined organic phase was dried
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-8ad61d17f5d042288f6a29ed579881dd
Source dataset
uspto-grants-2013_10
Patent number
US08546427B2

Reaction notes

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