Hydrazine hydrate (1:1) → 5-methylisoxazole-3-carbohydrazide

HRID 1786206Notes

Reaction equation

HRID 1786206 reaction equation
C[O:2][C:3]([C:5]1[CH:9]=[C:8]([CH3:10])[O:7][N:6]=1)=O.O.[NH2:12][NH2:13]>C(O)CCC>[CH3:10][C:8]1[O:7][N:6]=[C:5]([C:3]([NH:12][NH2:13])=[O:2])[CH:9]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 88245Methyl 5-methylisoxazole-3-carboxylate

Product 1

HCID 3282955-methylisoxazole-3-carbohydrazideYield 64%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

As described for example 112a, 5-methyl-isoxazole-3-carboxylic acid methyl ester in butanol was reacted with hydrazine hydrate (2 equivalents) at 100° C. for 2 h. Evaporation of all volatiles and chromatography (SiO2, dichloromethane:methanol:aq.ammonia (25%)=100:0:0 to 90:10:1) afforded the title compound as a white solid (yield: 64%). 1H-NMR (300 MHz, DMSO): δ=2.44 (d, J=1 Hz, 3H), 4.57 (s, 2H), 6.52 (d, J=1 Hz, 1H), 9.94 (s, 1H).

Workup

  1. customEvaporation of all volatiles and chromatography (SiO2, dichloromethane:methanol:aq.ammonia (25%)=100:0:0 to 90:10:1)

Sources & evidence

ORD record
ord-f35d3a094b984bff9a5653e5dad4fa95
Source dataset
uspto-grants-2009_03
Patent number
US07507729B2

Reaction notes

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