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

HRID 2239846Notes

Reaction equation

HRID 2239846 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) from 1a-1 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 Celite. The filtrate was concentrated in vacuo to give 3-Amino-1-(4-fluorophenyl)pyridin-2(1H)-one (530 mg, 100% yield) as a brown solid.

Workup

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

Sources & evidence

ORD record
ord-1cd20d39e7fe416c98bb25d52464358b
Source dataset
uspto-grants-2010_05
Patent number
US07723336B2

Reaction notes

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