Hydrazine hydrate (1:1) → 5-Methyl-3-isoxazoleacetic acid hydrazide

HRID 1786191Notes

Reaction equation

HRID 1786191 reaction equation
C[O:2][C:3](=O)[CH2:4][C:5]1[CH:9]=[C:8]([CH3:10])[O:7][N:6]=1.O.[NH2:13][NH2:14]>C(O)CCC>[CH3:10][C:8]1[O:7][N:6]=[C:5]([CH2:4][C:3]([NH:13][NH2:14])=[O:2])[CH:9]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 451179673-Isoxazoleacetic acid, 5-methyl-, methyl ester

Product 1

HCID 451179665-Methyl-3-isoxazoleacetic acid hydrazideYield 90%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

As described for example 112a, (5-methyl-isoxazol-3-yl)-acetic acid methyl ester in butanol was reacted with hydrazine hydrate (2 equivalents) and the resulting mixture was heated under reflux for 90 min. Evaporation of all volatiles afforded the title compound as a white solid (yield: 90%). 1H-NMR (300 MHz, DMSO): δ=2.36 (d, J=0.7 Hz, 3H), 3.39 (s, 2H), 4.25 (s, 2H), 6.13 (d, J=0.7 Hz, 1H), 9.27 (s, 1H).

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureunder reflux for 90 min
  3. customEvaporation of all volatiles

Sources & evidence

ORD record
ord-92db03ef5bef403a9021ddf50163f35d
Source dataset
uspto-grants-2009_03
Patent number
US07507729B2

Reaction notes

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