Hydrazine → 1-((3,5-dimethylisoxazol-4-yl)methyl)-1H-pyrazole-4-carbohydrazide

HRID 658672Notes

Reaction equation

HRID 658672 reaction equation
[CH3:1][C:2]1[C:6]([CH2:7][N:8]2[CH:12]=[C:11]([C:13](OCC)=[O:14])[CH:10]=[N:9]2)=[C:5]([CH3:18])[O:4][N:3]=1.[NH2:19][NH2:20]>CCO>[CH3:1][C:2]1[C:6]([CH2:7][N:8]2[CH:12]=[C:11]([C:13]([NH:19][NH2:20])=[O:14])[CH:10]=[N:9]2)=[C:5]([CH3:18])[O:4][N:3]=1

Participants

4

Reactant 2

HCID 9321HydrazineHCID 57944988Ethyl 1-((3,5-dimethylisoxazol-4-yl)methyl)-1H-pyrazole-4-carboxylate

Product 1

HCID 579449511-((3,5-dimethylisoxazol-4-yl)methyl)-1H-pyrazole-4-carbohydrazideYield 97.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Ethyl 1-((3,5-dimethylisoxazol-4-yl)methyl)-1H-pyrazole-4-carboxylate (example 10-1c) (6 g, 24 mmol) and hydrazine (7.5 g, 240 mmol) were stirred in EtOH (100 mL) at reflux for 12 hours. The solution was concentrated on the rotovap and the solid product was triturated with ethyl acetate/hexanes (1/9) and dried under high vacuum to afford 1-((3,5-dimethylisoxazol-4-yl)methyl)-1H-pyrazole-4-carbohydrazide (5.5 g, 97%) as a pure white solid. 1H NMR (DMSO-d6, 400 MHz): δ2.11 (s, 3H), 2.39 (s, 3H), 5.15 (s, 2H), 7.81 (s, 1H), 8.17 (s, 1H), 9.31 (bs, 1H).

Workup

  1. temperatureat reflux for 12 hours
  2. concentrationThe solution was concentrated on the rotovap
  3. customthe solid product was triturated with ethyl acetate/hexanes (1/9)
  4. customdried under high vacuum

Sources & evidence

ORD record
ord-b793a0d1eb6846dcb3ad7d6e2fe17063
Source dataset
uspto-grants-2011_12
Patent number
US08076491B2

Reaction notes

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