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

HRID 1376210Notes

Reaction equation

HRID 1376210 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-144df5b152584093a5ff6bfe76dd43d4
Source dataset
uspto-grants-2007_01
Patent number
US07169926B1

Reaction notes

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