Hydrazinecarboxaldehyde → 6219-52-9

HRID 1807198Notes

Reaction equation

HRID 1807198 reaction equation
Cl.CO[C:4](=[NH:14])[C:5]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][CH:6]=1.[CH:15]([NH:17][NH2:18])=O>N1C=CC=CC=1>[N+:11]([C:8]1[CH:7]=[CH:6][C:5]([C:4]2[NH:18][N:17]=[CH:15][N:14]=2)=[CH:10][CH:9]=1)([O-:13])=[O:12]

Participants

4

Reactant 2

HCID 12229HydrazinecarboxaldehydeHCID 12410479HCID 12410479, compound

Product 1

HCID 28252246219-52-9

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

4-Nitro-benzimidic acid methyl ester hydrochloride (635 mg, 2.93 mmol) was suspended in pyridine (7 mL) and formic hydrazide (Aldrich, 178 mg, 2.95 mmol) was added and the mixture was stirred at rt for 1 hr. The solvent was removed and the residue was dissolved in toluene (10 mL) and the mixture was stirred at reflux for 1.5 hrs. the mixture was cooled and water was added. The organic layer was separated and dried over sodium sulfate. The solvent was removed and the residue was suspended in 25% EtOAc/Hexanes and the solid was filtered to give a solid. 510 mg.

Workup

  1. customThe solvent was removed
  2. dissolutionthe residue was dissolved in toluene (10 mL)
  3. stirringthe mixture was stirred
  4. temperatureat reflux for 1.5 hrs
  5. temperaturethe mixture was cooled
  6. additionwater was added
  7. customThe organic layer was separated
  8. dry with materialdried over sodium sulfate
  9. customThe solvent was removed
  10. filtrationthe solid was filtered
  11. customto give a solid

Sources & evidence

ORD record
ord-e9d962c9286948cbac36aa0a6d7abc96
Source dataset
uspto-grants-2013_01
Patent number
US08354444B2

Reaction notes

Loading…