Ammonium Chloride → 3-amino-1-(4-fluorophenyl)pyridin-2(1H)-one

HRID 1361415Notes

Reaction equation

HRID 1361415 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH:13]=[CH:12][CH:11]=[C:10]([N+:14]([O-])=O)[C:9]2=[O:17])=[CH:4][CH:3]=1.[Cl-].[NH4+]>C1COCC1.CO.CCOC(C)=O.[Zn]>[NH2:14][C:10]1[C:9](=[O:17])[N:8]([C:5]2[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=2)[CH:13]=[CH:12][CH:11]=1

Participants

7

Reactant 2

HCID 25517Ammonium ChlorideHCID 58879966HCID 58879966, compound

Product 1

HCID 588799723-amino-1-(4-fluorophenyl)pyridin-2(1H)-oneYield 100%

Reagents, catalysts & solvents 4

HCID 23994ZincCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 1-(4-fluorophenyl)-3-nitropyridin-2(1H)-one (610 mg, 2.6 mmol) in THF (50 mL) and MeOH (50 mL), were added ammonium chloride (695 mg, 13.0 mmol, EMD) and Zn dust (850 mg, 13.0 mmol, Aldrich). The reaction mixture was stirred at room temperature for 3 h, diluted with 200 mL of EtOAc and filtered through a pad of Celitee. The filtrate was concentrated in vacuo to give the desired product (530 mg, 100% yield) as a brown solid. MS(ESI+) m/z 205.29 (M+H)+.

Workup

  1. filtrationfiltered through a pad of Celitee
  2. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-435e13b1e9d94afe85eda32820002c28
Source dataset
uspto-grants-2011_02
Patent number
US07880004B2

Reaction notes

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