Hydrazinecarboxaldehyde → HCID 178444665, compound

HRID 428926Notes

Reaction equation

HRID 428926 reaction equation
[CH2:1]([N:7]1[CH2:12][CH:11]2[CH:9]([C:10]2([C:14]2[CH:15]=[C:16]([C:20](=[NH:24])OCC)[CH:17]=[CH:18][CH:19]=2)[CH3:13])[C:8]1=[O:25])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].[CH:26]([NH:28][NH2:29])=O>CO>[CH2:1]([N:7]1[CH2:12][CH:11]2[CH:9]([C:10]2([CH3:13])[C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([C:20]3[NH:24][CH:26]=[N:28][N:29]=3)[CH:15]=2)[C:8]1=[O:25])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]

Participants

4

Reactant 2

HCID 12229HydrazinecarboxaldehydeHCID 22141159HCID 22141159, compound

Product 1

HCID 178444665HCID 178444665, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of crude ethyl 3-(3-hexyl-6-methyl-2-oxo-3-azabicyclo[3.1.0]hex-6-yl)benzenecarboximidoate (Preparation 42, 700 mg, 1.86 mmol) in methanol (5 ml) was added formic acid hydrazide (123 mg, 2.05 mmol) and the mixture was heated under reflux for 90 min. After cooling to room temperature, the solvent was removed in vacuo and the residue was heated to 150° C. for 12 h. The mixture was cooled and purified directly by silica column chromatography eluting with ethyl acetate:methanol (95:5) to afford the title compound (400 mg, 64%) as a colourless gum.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 90 min
  3. customthe solvent was removed in vacuo
  4. temperaturethe residue was heated to 150° C. for 12 h
  5. temperatureThe mixture was cooled
  6. custompurified directly by silica column chromatography
  7. washeluting with ethyl acetate:methanol (95:5)

Sources & evidence

ORD record
ord-b4b1706545094a3ea8c2a0c3e6c8de3f
Source dataset
uspto-grants-2001_11
Patent number
US06313312B1

Reaction notes

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