Ammonium Chloride → 1-(4-Aminophenyl)-1H-pyridin-2-one

HRID 1665660Notes

Reaction equation

HRID 1665660 reaction equation
[Cl-].[NH4+].[N+:3]([C:6]1[CH:11]=[CH:10][C:9]([N:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]2=[O:18])=[CH:8][CH:7]=1)([O-])=O>O.CO.C1COCC1.[Zn]>[NH2:3][C:6]1[CH:11]=[CH:10][C:9]([N:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]2=[O:18])=[CH:8][CH:7]=1

Participants

7

Reactant 2

HCID 25517Ammonium ChlorideHCID 101982881-(4-Nitrophenyl)-1H-pyridin-2-one

Product 1

HCID 115356951-(4-Aminophenyl)-1H-pyridin-2-oneYield 79.6%

Reagents, catalysts & solvents 4

HCID 23994ZincCatalystHCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Ammonium chloride (4.45 g, 83.26 mmol) in water (10 mL) and methanol (20 mL) was added to a stirred solution of 1-(4-nitro-phenyl)-1H-pyridin-2-one (1.8 g, 8.3 mmol) in THF (20 mL). Zinc powder (4.3 g, 66.6 mmol) was then added portion wise and the resulting mixture was stirred at room temperature for 30 minutes. The mixture was filtered over celite and the filtrate was concentrated and extracted with ethyl acetate. The organic layer was washed with brine solution, dried over Na2SO4 and concentrated to afford 1.23 g (79%) of 1-(4-amino-phenyl)-1H-pyridin-2-one. 1H NMR: (DMSO-d6): δ 7.6-7.4 (m, 2H), 7.0 (d, 2H), 6.7 (d, 2H), 6.45 (d, 1H), 6.3 (t, 1H), 5.4 (s, 2H).

Workup

  1. filtrationThe mixture was filtered over celite
  2. concentrationthe filtrate was concentrated
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with brine solution
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-2d466c8e753b400f87200e5dfdb91d0a
Source dataset
uspto-grants-2011_10
Patent number
US08039463B2

Reaction notes

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