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

HRID 2244805Notes

Reaction equation

HRID 2244805 reaction equation
Cl[C:2]1[CH:7]=[CH:6][N:5]([CH2:8][CH3:9])[C:4](=[O:10])[C:3]=1[N+:11]([O-:13])=[O:12].[NH3:14]>C1COCC1>[NH2:14][C:2]1[CH:7]=[CH:6][N:5]([CH2:8][CH3:9])[C:4](=[O:10])[C:3]=1[N+:11]([O-:13])=[O:12]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 714223354-chloro-1-ethyl-3-nitro-1H-pyridin-2-one

Product 1

HCID 714223344-amino-1-ethyl-3-nitro-1H-pyridin-2-oneYield 75.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 4-chloro-1-ethyl-3-nitro-1H-pyridin-2-one (1.40 g, 6.91 mmol) and 28% aqueous ammonia (6.92 g, 55.3 mmol) in THF (30 mL) was stirred at room temperature for 17 h. The solvent was evaporated under reduced pressure and water was added to the residue. The resulting precipitate was filtered and washed with water to give 4-amino-1-ethyl-3-nitro-1H-pyridin-2-one (0.95 g, 75% yield). 1H-NMR (DMSO): δ, 8.03 (m, 2H), 7.57 (d, 1H, J=7.2 Hz), 5.90 (d, 1H, J=7.2 Hz), 3.78 (q, 2H, J=7.2 Hz), 1.15 (t, 3H, J=7.2 Hz). MS: calculated for C7H7N3O3+H 184.1; found: 184.1.

Workup

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

Sources & evidence

ORD record
ord-e0360a508b914fb6a75003ab231b0b57
Source dataset
uspto-grants-2010_03
Patent number
US07678909B1

Reaction notes

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