Methanol → 3-Amino-5-nitropyridin-2(1H)-one

HRID 66361

Reaction equation

HRID 66361 reaction equation
[N+:1]([C:4]1[C:5](=[O:13])[NH:6][CH:7]=[C:8]([N+:10]([O-:12])=[O:11])[CH:9]=1)([O-])=O.CO.[OH-].[NH4+].O.O.O.O.O.O.O.O.O.[S-2].[Na+].[Na+]>O>[NH2:1][C:4]1[C:5](=[O:13])[NH:6][CH:7]=[C:8]([N+:10]([O-:12])=[O:11])[CH:9]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 14923Ammonium HydroxideHCID 73972Sodium sulfide nonahydrateHCID 763242(1H)-Pyridinone, 3,5-dinitro-

Product 1

HCID 227547823-Amino-5-nitropyridin-2(1H)-one

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 5.5 g. of 3,5-dinitro-2-pyridone in 200 ml. of methanol was adjusted to pH 8 with ammonium hydroxide. At 60-65° C., there was added slowly a solution of 10.8 g. of sodium sulfide nonahydrate in 30 ml. of water. After 1 hour at 60-65° C. the solvent was evaporated and the residue was extracted with hot benzene and acetic acid to neutralize any sodium salt. The benzene was decanted and cooled to give a precipitate. Recrystallization from methanol gave 3-amino-5-nitro-2-pyridone, m.p. 200°-201° C.

Workup

  1. additionAt 60-65° C., there was added slowly a solution of 10.8 g
  2. customAfter 1 hour at 60-65° C. the solvent was evaporated
  3. extractionthe residue was extracted with hot benzene and acetic acid
  4. customThe benzene was decanted
  5. temperaturecooled
  6. customto give a precipitate
  7. customRecrystallization from methanol

Sources & evidence

ORD record
ord-2fa70162e10541fb943089f50b6b7a29
Source dataset
uspto-grants-1978_12
Patent number
US04131677

Linked notes

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