Hydrazine hydrate (1:1) → 2-(5-methyl-1H-pyrazol-1-yl)acetohydrazide

HRID 1786198Notes

Reaction equation

HRID 1786198 reaction equation
C([O:3][C:4](=O)[CH2:5][N:6]1[C:10]([CH3:11])=[CH:9][CH:8]=[N:7]1)C.O.[NH2:14][NH2:15]>C(O)C>[CH3:11][C:10]1[N:6]([CH2:5][C:4]([NH:14][NH2:15])=[O:3])[N:7]=[CH:8][CH:9]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 4039589(5-Methyl-pyrazol-1-yl)-acetic acid ethyl ester

Product 1

HCID 70184052-(5-methyl-1H-pyrazol-1-yl)acetohydrazideYield 95%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

As described for example 112a, (5-methyl-pyrazol-1-yl)-acetic acid ethyl ester in ethanol was reacted with hydrazine hydrate (2 equivalents) and the resulting mixture was heated under reflux for 8 h. The mixture was cooled to rt and the precipitated product was filtered off, dried and crystallized from toluene. The title compound (95% purity, based on NMR) was obtained as a white solid (yield: 45%). 1H-NMR (300 MHz, DMSO): δ=2.24 (s, 3H), 4.29 (s, 2H), 4.65 (s, 2H), 6.00 (d, J=1 Hz, 1H), 7.55 (d, J=1 Hz, 1H), 9.27 (s, 1H).

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureunder reflux for 8 h
  3. filtrationthe precipitated product was filtered off
  4. customdried
  5. customcrystallized from toluene

Sources & evidence

ORD record
ord-5397f43a2b4c41b0bcaf62759bb6b2b8
Source dataset
uspto-grants-2009_03
Patent number
US07507729B2

Reaction notes

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