3-Acetylpyridine → HCID 59898042, compound

HRID 428951Notes

Reaction equation

HRID 428951 reaction equation
[C:1]([C:4]1[CH:5]=[N:6][CH:7]=[CH:8][CH:9]=1)(=O)[CH3:2].O.O.[NH2:12][NH2:13]>O>[N:6]1[CH:7]=[CH:8][CH:9]=[C:4]([C:1](=[N:12][NH2:13])[CH3:2])[CH:5]=1

Participants

4

Reactant 2

HCID 95893-AcetylpyridineHCID 22141362Hydrazine--water (1/2)

Product 1

HCID 59898042HCID 59898042, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 3-acetylpyridine (6.1 g, 52 mmol) in industrial methylated spirits (50 ml) was added dropwise hydrazine hydrate monohydrate (3.11 ml, 0.1 mol). The reaction mixture was refluxed for 4 h, before cooling to room temperature and stirring for 16 h. Water (25 ml) was added and the volatile organics were removed in vacuo. The predominantly aqueous residual liquor was extracted with ethyl acetate, and the combined organic extracts were dried (Na2SO4) and concentrated to give a yellow oil (5.4 g, 80%) which was taken forward without further purification.

Workup

  1. temperatureThe reaction mixture was refluxed for 4 h
  2. customthe volatile organics were removed in vacuo
  3. extractionThe predominantly aqueous residual liquor was extracted with ethyl acetate
  4. dry with materialthe combined organic extracts were dried (Na2SO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-038c360d8d524b7cae77a7c6c57cefe8
Source dataset
uspto-grants-2001_11
Patent number
US06313312B1

Reaction notes

Loading…