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

HRID 280465Notes

Reaction equation

HRID 280465 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° C.-107° C.

Workup

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

Sources & evidence

ORD record
ord-f3d63ef7582f414aa4282875d87cf37e
Source dataset
uspto-grants-1986_05
Patent number
US04589905

Reaction notes

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