Hydroxyamine hydrochloride → HCID 13732605, compound

HRID 542563Notes

Reaction equation

HRID 542563 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]([O:20][CH3:21])=[CH:16][CH:15]=3)[C:11]([OH:12])=[C:6]2[CH:5]=[N:4]1)[CH3:2].Cl.[NH2:24]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]([O:20][CH3:21])=[CH:16][CH:15]=4)=[N:24][O:12][C:11]3=[C:6]2[CH:5]=[N:4]1)[CH3:2]

Participants

4

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 178463028HCID 178463028, compound

Product 1

HCID 13732605HCID 13732605, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

1-Ethyl-4-hydroxy-5-(4-methoxybenzoyl)-1H-pyrazolo[3,4-b]pyridine (3.60 g) was refluxed overnight in 30 ml of pyridine containing 4.0 g of hydroxylamine hydrochloride. At the end of this time the pyridine was evaporated and the residue triturated with 5% hydrochloric acid. The product obtained in this manner was chromatographed silica gel (5% methanol/dichloromethane) to remove a fluorescent impurity. Combination of the appropriate fractions and recrystallization from dichloromethane/hexane gave 2.95 g of pure product, mp 156°-157° C.

Workup

  1. customAt the end of this time the pyridine was evaporated
  2. customthe residue triturated with 5% hydrochloric acid
  3. customThe product obtained in this manner
  4. customwas chromatographed silica gel (5% methanol/dichloromethane)
  5. customto remove a fluorescent impurity
  6. customCombination of the appropriate fractions and recrystallization from dichloromethane/hexane

Sources & evidence

ORD record
ord-aae0c69ac18441c4b39ccffe40a35924
Source dataset
uspto-grants-1987_04
Patent number
US04658029

Reaction notes

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