Hydroxyamine hydrochloride → HCID 13749199, compound

HRID 1732004Notes

Reaction equation

HRID 1732004 reaction equation
Cl[C:2]1[C:7]([C:8](=[O:16])[C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([Cl:15])[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.[Na+]>C(O)(=O)C>[Cl:15][C:11]1[CH:10]=[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:14]=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 443297Hydroxyamine hydrochloride2×HCID 517045Sodium AcetateHCID 14171314HCID 14171314, compound

Product 1

HCID 13749199HCID 13749199, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

4-Chloro-5-(3-chlorobenzoyl)-1-ethyl-1H-pyrazolo[3,4-b]pyridine (2.65 g) was stirred overnight at 90° in 75 ml of glacial acetic acid containing 3.0 g of hydroxylamine hydrochloride. Sodium acetate (3.5 g) was then added, followed by an additional 1.0 g of hydroxylamine hydrochloride. The reaction mixture was then evaporated and the residue distributed between aqueous sodium bicarbonate and dichloromethane. The organic layer was evaporated and the residue was triturated with methanol and then chromatographed (230-400 mesh silica gel, 10% ethyl acetate/dichloromethane) to give 1.20 g of product, mp 207°-209°. It was combined with the products of several other runs and recrystallized from ethyl acetate to give analytically pure material, mp 209°-210° C.

Workup

  1. customThe reaction mixture was then evaporated
  2. customThe organic layer was evaporated
  3. customthe residue was triturated with methanol
  4. customchromatographed (230-400 mesh silica gel, 10% ethyl acetate/dichloromethane)

Sources & evidence

ORD record
ord-67419644fc924d489c4201a7630242fc
Source dataset
uspto-grants-1986_11
Patent number
US04624955

Reaction notes

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