Water → N'-(5-nitropyridin-2-yl)acetohydrazide

HRID 1979605Notes

Reaction equation

HRID 1979605 reaction equation
[C:1](Cl)(=[O:3])[CH3:2].[NH:5]([C:7]1[CH:12]=[CH:11][C:10]([N+:13]([O-:15])=[O:14])=[CH:9][N:8]=1)[NH2:6].N1C=CC=CC=1.O>O1CCCC1>[N+:13]([C:10]1[CH:11]=[CH:12][C:7]([NH:5][NH:6][C:1](=[O:3])[CH3:2])=[N:8][CH:9]=1)([O-:15])=[O:14]

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 6367Acetyl chlorideHCID 40319312-Hydrazinyl-5-nitropyridine

Product 1

HCID 4274094N'-(5-nitropyridin-2-yl)acetohydrazide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Acetyl chloride (0.51 g, 6.5 mmole) was added dropwise to a stirred solution of 2-hydrazino-5-nitropyridine (1.0 g, 6.5 mmole) in tetrahydrofuran (20 ml). Pyridine (0.51 g, 6.5 mmole) was added, the mixture stirred for 0.5 h, and then poured into water (200 ml). The aqueous solution was extracted with ethyl actate, the extract dried (MgSO4) and the solvent removed under reduced pressure. Recrystallisation of the residue from 1,2-dichloroethane afforded the pure product, 1.1 g, 86%, as a cream coloured solid, m.p. 226°-227° C.

Workup

  1. extractionThe aqueous solution was extracted with ethyl actate
  2. dry with materialthe extract dried (MgSO4)
  3. customthe solvent removed under reduced pressure
  4. customRecrystallisation of the residue from 1,2-dichloroethane
  5. customafforded the pure product, 1.1 g, 86%

Sources & evidence

ORD record
ord-57e7e94e215a49adb727353a993960cf
Source dataset
uspto-grants-1984_11
Patent number
US04481268

Reaction notes

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