Hydrazine hydrate (1:1) → HCID 67549766, compound

HRID 1786190Notes

Reaction equation

HRID 1786190 reaction equation
C[O:2][C:3](=O)[CH2:4][C:5]1[O:9][N:8]=[CH:7][CH:6]=1.O.[NH2:12][NH2:13]>C(O)CCC>[O:9]1[C:5]([CH2:4][C:3]([NH:12][NH2:13])=[O:2])=[CH:6][CH:7]=[N:8]1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 54297626HCID 54297626, compound

Product 1

HCID 67549766HCID 67549766, compoundYield 41%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

As described for example 112a, isoxazol-5-yl-acetic acid methyl ester in butanol was reacted with hydrazine hydrate (2 equivalents) and the resulting mixture was heated under reflux for 4 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: 41%). 1H-NMR (300 MHz, DMSO): δ=3.65 (s, 2H), 4.31 (s, 2H), 6.32 (s, 1H), 8.46 (s, 1H), 9.32 (s, 1H).

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureunder reflux for 4 h
  3. customEvaporation of all volatiles and chromatography (SiO2, dichloromethane:methanol:aq.ammonia (25%)=100:0:0 to 90:10:1)

Sources & evidence

ORD record
ord-12fafd759ff24cf8b857870d0ddfbd33
Source dataset
uspto-grants-2009_03
Patent number
US07507729B2

Reaction notes

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