HCID 67290469, compound → HCID 67290159, compound

HRID 1036892Notes

Reaction equation

HRID 1036892 reaction equation
[CH3:1][C:2]1([CH3:23])[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([C:12]#[N:13])[CH:10]=2)[NH:5][CH:4]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[N+:20]([O-])=O)[CH2:3]1>[Cl-].[NH4+].C(O)C.[Fe]>[NH2:20][C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=1[CH:4]1[CH2:3][C:2]([CH3:1])([CH3:23])[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([C:12]#[N:13])[CH:10]=2)[NH:5]1

Participants

5

Reactant 1

HCID 67290469HCID 67290469, compound

Product 1

HCID 67290159HCID 67290159, compoundYield 56%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 702EthanolSolventHCID 25517Ammonium ChlorideSolvent

Procedure

To a suspension of 4,4-dimethyl-2-(2-nitrophenyl)-1,2,3,4-tetrahydroquinoline-6-carbonitrile (2 g, 6.54 mmol) in saturated aqueous ammonium chloride and ethanol was added iron powder 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-(2-aminophenyl)-4,4-dimethyl-1,2,3,4-tetrahydroquinoline-6-carbonitrile as white solid (1 g, yield 56%). The product was used for the next step without further purification. LC/MS m/e obsd. (ESI+) [(M+H)+] 228.2.

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-727521cbcf9a4a5ca1f262b4f503eb3d
Source dataset
uspto-grants-2013_10
Patent number
US08546427B2

Reaction notes

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