Hydroxyamine hydrochloride → HCID 13749200, compound

HRID 1732005Notes

Reaction equation

HRID 1732005 reaction equation
Cl[C:2]1[C:7]([C:8](=[O:16])[C:9]2[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][CH:10]=2)=[CH:6][N:5]=[C:4]2[N:17]([CH2:20][CH3:21])[N:18]=[CH:19][C:3]=12.Cl.[NH2:23]O>C(O)(=O)C>[Cl:15][C:12]1[CH:13]=[CH:14][C:9]([C:8]2[O:16][N:23]=[C:2]3[C:7]=2[CH:6]=[N:5][C:4]2[N:17]([CH2:20][CH3:21])[N:18]=[CH:19][C:3]3=2)=[CH:10][CH:11]=1

Participants

4

Reactant 2

HCID 443297Hydroxyamine hydrochloride2×HCID 14171315HCID 14171315, compound

Product 1

HCID 13749200HCID 13749200, compoundYield 43%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

4-Chloro-5-(4-chlorobenzoyl)-1-ethyl-1H-pyrazolo[3,4-b]pyridine (3.76 g) was suspended in 75 ml of glacial acetic acid, and to this was added 1.05 g of hydroxylamine hydrochloride. The reaction mixture was stirred overnight at 80° and the next morning yet another 1.05 g of hydroxylamine hydrochloride was added. After stirring the mixture for additional two hours the solvent was evaporated and the residue washed first with sodium bicarbonate solution and then methanol. The resulting product was then chromatographed over 230-400 mesh silica gel (10% ethyl acetate/dichloromethane), giving 1.51 g of product, mp 248°-250° C.

Workup

  1. stirringAfter stirring the mixture for additional two hours the solvent
  2. customwas evaporated
  3. washthe residue washed first with sodium bicarbonate solution
  4. customThe resulting product was then chromatographed over 230-400 mesh silica gel (10% ethyl acetate/dichloromethane)

Sources & evidence

ORD record
ord-e7b705397cd44d3d9327ac1a9842fd40
Source dataset
uspto-grants-1986_11
Patent number
US04624955

Reaction notes

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