Hydrazine hydrate (1:1) → N-[4-(3-Fluoro-benzyloxy)-phenyl]-2-hydrazinocarbonyl-acetamide

HRID 1884134Notes

Reaction equation

HRID 1884134 reaction equation
C[O:2][C:3](=O)[CH2:4][C:5]([NH:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([F:22])[CH:17]=2)=[CH:10][CH:9]=1)=[O:6].O.[NH2:25][NH2:26]>CO>[F:22][C:18]1[CH:17]=[C:16]([CH:21]=[CH:20][CH:19]=1)[CH2:15][O:14][C:11]1[CH:12]=[CH:13][C:8]([NH:7][C:5](=[O:6])[CH2:4][C:3]([NH:25][NH2:26])=[O:2])=[CH:9][CH:10]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)2×HCID 10335956N-[4-(3-fluoro-benzyloxy)-phenyl]-malonamic acid methyl ester

Product 1

HCID 22137967N-[4-(3-Fluoro-benzyloxy)-phenyl]-2-hydrazinocarbonyl-acetamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A suspension of 0.35 g (1.1 mmol) of N-[4-(3-fluoro-benzyloxy)-phenyl]-malonamic acid methyl ester in 7 ml methanol is treated with 83 mg (1.7 mmol) of hydrazine hydrate. The reaction mixture is refluxed for 2 h, then another portion of 300 mg (6 mmol) of hydrazine hydrate is added and reflux is pursued for another 8 h. The mixture is cooled and hold overnight in the frig. The precipitate is filtered off and recrystallised from methanol to yield 0.043 g (12%) of filthy, colorless needles. MS: m/e=318.3 (M++H).

Workup

  1. temperatureThe reaction mixture is refluxed for 2 h
  2. temperaturereflux
  3. temperatureThe mixture is cooled
  4. waithold overnight in the frig
  5. filtrationThe precipitate is filtered off
  6. customrecrystallised from methanol
  7. customto yield 0.043 g (12%) of filthy, colorless needles

Sources & evidence

ORD record
ord-c0489d54dc4c477ba6e3e5ecabf3ac32
Source dataset
uspto-grants-2004_07
Patent number
US06762320B2

Reaction notes

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