Ammonia → 4-amino-6-isopropyl-3-nitro-1H-pyridin-2-one

HRID 1988734Notes

Reaction equation

HRID 1988734 reaction equation
Cl[C:2]1[CH:7]=[C:6]([CH:8]([CH3:10])[CH3:9])[NH:5][C:4](=[O:11])[C:3]=1[N+:12]([O-:14])=[O:13].[NH3:15]>CO>[NH2:15][C:2]1[CH:7]=[C:6]([CH:8]([CH3:10])[CH3:9])[NH:5][C:4](=[O:11])[C:3]=1[N+:12]([O-:14])=[O:13]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 223800994-Chloro-6-isopropyl-3-nitro-1H-pyridin-2-one

Product 1

HCID 223799674-amino-6-isopropyl-3-nitro-1H-pyridin-2-one

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 4-chloro-6-isopropyl-3-nitro-1H-pyridin-2-one (700 mg, 3.23 mmol) in 6-7 μL of 7 N NH3 in MeOH is stirred at 100° C. in a sealed tube for 1.5 h. After cooling, the reaction mixture is concentrated in vacuo. The residue is suspended in H2O, filtered, washed with H2O, and dried, yielding 4-amino-6-isopropyl-3-nitro-1H-pyridin-2-one. 1H NMR (DMSO-d6, 300 MHz) δ 10.96 (br s, 1H), 8.15 (br s, 2H), 5.70 (d, J=0.9 Hz, 1H), 2.58 (sept, J=6.9 Hz, 1H), 1.11 (d, J=6.9 Hz, 6H) ppm.

Workup

  1. temperatureAfter cooling
  2. concentrationthe reaction mixture is concentrated in vacuo
  3. filtrationfiltered
  4. washwashed with H2O
  5. customdried

Sources & evidence

ORD record
ord-bbd5bbb5fbbf45dc84a9a12ef7509ac6
Source dataset
uspto-grants-2010_01
Patent number
US07642267B2

Reaction notes

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