Acetohydrazide → HCID 140606545, compound

HRID 920942Notes

Reaction equation

HRID 920942 reaction equation
[Cl:1][C:2]1[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[C:6]([CH:13]=O)[N:5]=[CH:4][CH:3]=1.[C:15]([NH:18][NH2:19])(=[O:17])[CH3:16]>C(O)C>[C:15]([NH:18]/[N:19]=[CH:13]/[C:6]1[N:5]=[CH:4][CH:3]=[C:2]([Cl:1])[C:7]=1[C:8]([O:10][CH2:11][CH3:12])=[O:9])(=[O:17])[CH3:16]

Participants

4

Reactant 2

HCID 14039AcetohydrazideHCID 866831573-Pyridinecarboxylic acid, 4-chloro-2-formyl-, ethyl ester

Product 1

HCID 140606545HCID 140606545, compoundYield 73.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To 2.1 g (9.83 mmol) of ethyl 4-chloro-2-formylnicotinate in 60 mL of ethanol was added 0.874 g (11.80 mmol) of acetohydrazide at room temperature. Then, the reaction mixture was heated under reflux for 2 h. The reaction mixture was extracted with water/DCM. The organic phase was washed with brine, dried, filtrated and concentrated to give 1.95 g (73.6%) of the title compound as white solid.

Workup

  1. temperatureThen, the reaction mixture was heated
  2. temperatureunder reflux for 2 h
  3. extractionThe reaction mixture was extracted with water/DCM
  4. washThe organic phase was washed with brine
  5. customdried
  6. filtrationfiltrated
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-d101b573c95e46b892a69e7c707ecee8
Source dataset
uspto-grants-2016_03
Patent number
US09273068B2

Reaction notes

Loading…