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

HRID 1166062Notes

Reaction equation

HRID 1166062 reaction equation
[CH3:1][C:2]1[O:6][N:5]=[C:4]([C:7]([O:9]CC)=O)[CH:3]=1.O.[NH2:13][NH2:14]>CO>[CH3:1][C:2]1[O:6][N:5]=[C:4]([C:7]([NH:13][NH2:14])=[O:9])[CH:3]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 76677Ethyl 5-methylisoxazole-3-carboxylate

Product 1

HCID 3282955-methylisoxazole-3-carbohydrazideYield 29.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of ethyl 5-methylisoxazole-3-carboxylate (3.0 g, 19 mmol) in methanol (30 ml) at 0° C. under nitrogen was added hydrazine hydrate (3.04 g, 95 mmol) over 0.3 h. The reaction was stirred at 0° C. for 0.25 h and at RT for 1 h. The white precipitate was filtered off and washed with methanol to give the title-compound (0.78 g, 29%) as a white solid, 1H NMR (250 MHz, CDCl3) δ 2.41 (3H, d, J=0.8 Hz, CH3), 4.07 (2H, br s, NH2), 6.44 (1H, q, J=0.8 Hz, Ar—H), 7.99 (1H, br s, N—H); MS (ES+) m/e 142 [MH]+.

Workup

  1. filtrationThe white precipitate was filtered off
  2. washwashed with methanol

Sources & evidence

ORD record
ord-976527f483ab415fba5d0ade9bec5d22
Source dataset
uspto-grants-2003_09
Patent number
US06613766B1

Reaction notes

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