Ammonia → 4-amino-1-benzyl-3-nitro-1H-pyridin-2-one

HRID 2244798Notes

Reaction equation

HRID 2244798 reaction equation
[CH2:1]([N:8]1[CH:13]=[CH:12][C:11](Cl)=[C:10]([N+:15]([O-:17])=[O:16])[C:9]1=[O:18])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH3:19]>C1COCC1>[NH2:19][C:11]1[CH:12]=[CH:13][N:8]([CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[C:9](=[O:18])[C:10]=1[N+:15]([O-:17])=[O:16]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 249444631-Benzyl-4-chloro-3-nitropyridin-2(1H)-one

Product 1

HCID 219476414-amino-1-benzyl-3-nitro-1H-pyridin-2-oneYield 91.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 1-benzyl-4-chloro-3-nitro-1H-pyridin-2-one (1.30 g, 4.91 mmol) and 28% aqueous ammonia (4.92 g, 39.3 mmol) in THF (30 mL) was stirred at room temp for 17 h. The solvent was evaporated under reduced pressure and water was added to the residue. The resulting precipitate was collected by filtration, and washed with water to give 4-amino-1-benzyl-3-nitro-1H-pyridin-2-one (1.10 g, 91% yield). 1H-NMR (DMSO): δ 8.13 (m, 2H), 7.69 (d, 1H, J=8.0 Hz), 7.31 (m, 5H), 5.94 (d, 1H, J=8.0 Hz), 4.96 (s, 2H). MS: calculated for C12H11N3O3+H 246.1; found: 246.2.

Workup

  1. customThe solvent was evaporated under reduced pressure and water
  2. additionwas added to the residue
  3. filtrationThe resulting precipitate was collected by filtration
  4. washwashed with water

Sources & evidence

ORD record
ord-f2d90cb5b571474bbff89728ef727d9b
Source dataset
uspto-grants-2010_03
Patent number
US07678909B1

Reaction notes

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