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Hydrazine hydrate (1:1) → 2-(3,5-Dimethyl-1H-pyrazol-4-yl)acetohydrazide

HRID 1786193
Notes
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Reaction equation

HRID 1786193 reaction equation
C([O:3][C:4](=O)[CH2:5][C:6]1[C:7]([CH3:12])=[N:8][NH:9][C:10]=1[CH3:11])C.[NH:14]1C=C(CC(O)=O)C=[N:15]1.O.NN>C(O)CCC>[CH3:12][C:7]1[C:6]([CH2:5][C:4]([NH:14][NH2:15])=[O:3])=[C:10]([CH3:11])[NH:9][N:8]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 24654Hydrazine hydrate (1:1)HCID 16394806ethyl 2-(3,5-dimethyl-1H-pyrazol-4-yl)acetateHCID 205553512-(1H-pyrazol-4-yl)acetic acid

Product 1

HCID 432366912-(3,5-Dimethyl-1H-pyrazol-4-yl)acetohydrazideYield 68%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

As described for example 112a, (3,5-dimethyl-1H-pyrazol-4-yl)-acetic acid ethyl ester (Rainer, Georg. 4-Pyrazoleacetic acid derivatives. U.S. (1979), U.S. Pat. No. 4,146,721) in butanol was reacted with hydrazine hydrate (3 equivalents) and the resulting mixture was heated under reflux for 6 h. Evaporation of all volatiles afforded the title compound as a colourless oil (yield: 68%). MS: m/e=183.3 [M+H]+.

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureunder reflux for 6 h
  3. customEvaporation of all volatiles

Sources & evidence

ORD record
ord-631d905e8e454e15aa32371b58415fcf
Source dataset
uspto-grants-2009_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07507729B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes