Hydroxyamine hydrochloride → methyl 1-(3-chloropyridin-2-yl)-3-[(hydroxyimino)methyl]-1H-pyrazole-5-carboxylate

HRID 1630669Notes

Reaction equation

HRID 1630669 reaction equation
[Cl:1][C:2]1[C:3]([N:8]2[C:12]([C:13]([O:15][CH3:16])=[O:14])=[CH:11][C:10]([CH:17]=O)=[N:9]2)=[N:4][CH:5]=[CH:6][CH:7]=1.Cl.[NH2:20][OH:21].C([O-])(=O)C.[Na+]>C(O)C.O.C(OC)(C)(C)C>[Cl:1][C:2]1[C:3]([N:8]2[C:12]([C:13]([O:15][CH3:16])=[O:14])=[CH:11][C:10]([CH:17]=[N:20][OH:21])=[N:9]2)=[N:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 86661390HCID 86661390, compound

Product 1

HCID 136407523methyl 1-(3-chloropyridin-2-yl)-3-[(hydroxyimino)methyl]-1H-pyrazole-5-carboxylate

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 15413tert-Butyl methyl etherSolvent

Procedure

Methyl 1-(3-chloropyridin-2-yl)-3-formyl-1H-pyrazole-5-carboxylate (0.99 g), hydroxylamine hydrochloride (0.39 g) and sodium acetate (0.61 g) were stirred at RT in a mixture of 5 ml of ethanol and 3 ml of water for 30 min. The mixture was diluted with methyl tert-butyl ether, washed with saturated sodium chloride solution and dried over sodium sulphate. Distillative removal of the solvent gave the desired target product.

Workup

  1. washwashed with saturated sodium chloride solution
  2. dry with materialdried over sodium sulphate
  3. customDistillative removal of the solvent
  4. customgave the desired target product

Sources & evidence

ORD record
ord-82c8cfae78df4abc95c5f024c597ce50
Source dataset
uspto-grants-2014_07
Patent number
US08791139B2

Reaction notes

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