Hydroxyamine hydrochloride → 5-(hydroxyiminomethyl)-1-tert-butyl-1H-pyrazole-4-carboxylic acid, ethyl ester

HRID 1249447Notes

Reaction equation

HRID 1249447 reaction equation
Cl.[NH2:2][OH:3].[CH:4]([C:6]1[N:10]([C:11]([CH3:14])([CH3:13])[CH3:12])[N:9]=[CH:8][C:7]=1[C:15]([O:17][CH2:18][CH3:19])=[O:16])=O>C(O)C>[OH:3][N:2]=[CH:4][C:6]1[N:10]([C:11]([CH3:14])([CH3:13])[CH3:12])[N:9]=[CH:8][C:7]=1[C:15]([O:17][CH2:18][CH3:19])=[O:16]

Participants

4

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 136541795-formyl-1-tert-butyl-1H-pyrazole-4-carboxylic acid, ethyl ester

Product 1

HCID 1363321415-(hydroxyiminomethyl)-1-tert-butyl-1H-pyrazole-4-carboxylic acid, ethyl esterYield 40.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Hydroxylamine hydrochloride (4.3 grams, 0.062 mole) was added to a cold solution of 5-formyl-1-tert-butyl-1H-pyrazole-4-carboxylic acid, ethyl ester (7 grams, 0.031 mole) in absolute ethanol (40 ml.). The reaction mixture was stirred in the cold for thirty minutes, then at room temperature for 16 hours. The reaction mixture was then poured over ice-water, and the precipitated product was separated, dried, and recrystallized from toluene, yielding 3 grams of 5-(hydroxyiminomethyl)-1-tert-butyl-1H-pyrazole-4-carboxylic acid, ethyl ester, m.p., 105°-107° C.

Workup

  1. customthe precipitated product was separated
  2. customdried
  3. customrecrystallized from toluene

Sources & evidence

ORD record
ord-e1f820c6ef5548b8a7a77429edd4b342
Source dataset
uspto-grants-1986_12
Patent number
US04631343

Reaction notes

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