Hydroxyamine hydrochloride → HCID 13732601, compound

HRID 1731527Notes

Reaction equation

HRID 1731527 reaction equation
[CH2:1]([N:3]1[C:7]2=[N:8][CH:9]=[C:10]([C:13](=O)[C:14]3[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=3)[C:11]([OH:12])=[C:6]2[CH:5]=[N:4]1)[CH3:2].Cl.[NH2:23]O>N1C=CC=CC=1>[CH2:1]([N:3]1[C:7]2=[N:8][CH:9]=[C:10]3[C:13]([C:14]4[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=4)=[N:23][O:12][C:11]3=[C:6]2[CH:5]=[N:4]1)[CH3:2]

Participants

4

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 178463027HCID 178463027, compound

Product 1

HCID 13732601HCID 13732601, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

1-Ethyl-5-(4-fluorobenzoyl)-4-hydroxy-1H-pyrazolo[3,4-b]pyridine (3.35 g) was refluxed overnight in 75 ml of pyridine containing 4.0 g of hydroxylamine hydrochloride. The solvent was then evaporated and the residue triturated with 5% hydrochloric acid The product thus obtained was washed with methanol and then chromatographed over silica gel (5% methanol/dichloromethane) to remove a trace of fluorescent impurity. After recrystallization from ethyl acetate/hexane, 2.83 g of product was obtained, mp 175°-176° C.

Workup

  1. customThe solvent was then evaporated
  2. customthe residue triturated with 5% hydrochloric acid The product
  3. customthus obtained
  4. washwas washed with methanol
  5. customchromatographed over silica gel (5% methanol/dichloromethane)
  6. customto remove a trace of fluorescent impurity
  7. customAfter recrystallization from ethyl acetate/hexane

Sources & evidence

ORD record
ord-edf2e65a8e134634837492fdc18c731c
Source dataset
uspto-grants-1986_11
Patent number
US04622326

Reaction notes

Loading…