Water → HCID 13749206, compound

HRID 1732011Notes

Reaction equation

HRID 1732011 reaction equation
Cl[C:2]1[C:7]([C:8](=[O:17])[C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([O:15][CH3:16])[CH:10]=2)=[CH:6][N:5]=[C:4]2[N:18]([CH2:21][CH3:22])[N:19]=[CH:20][C:3]=12.Cl.[NH2:24]O.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.O>C(O)(=O)C>[CH2:21]([N:18]1[C:4]2[N:5]=[CH:6][C:7]3[C:2](=[N:24][O:17][C:8]=3[C:9]3[CH:14]=[CH:13][CH:12]=[C:11]([O:15][CH3:16])[CH:10]=3)[C:3]=2[CH:20]=[N:19]1)[CH3:22]

Participants

6

Reactant 4

HCID 962WaterHCID 443297Hydroxyamine hydrochlorideHCID 521998p-Toluenesulfonic acid monohydrateHCID 14171322HCID 14171322, compound

Product 1

HCID 13749206HCID 13749206, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Five grams of 4-chloro-1-ethyl-5-(3-methoxybenzoyl)-1H-pyrazolo[3,4-b]pyridine was refluxed for 2 hours in 500 ml of acetic acid containing 15 g of hydroxylamine hydrochloride and 1 g of p-toluenesulfonic acid monohydrate. At the end of this time the reaction mixture was poured into water and extracted with dichloromethane. The organic phase was washed well with water, dried, evaporated and chromatographed over 230-400 mesh silica gel. The appropriate fractions were combined and evaporated to give 3.05 g of product, mp 170°-171°. After recrystallization from water it had mp 169°-171° C.

Workup

  1. extractionextracted with dichloromethane
  2. washThe organic phase was washed well with water
  3. customdried
  4. customevaporated
  5. customchromatographed over 230-400 mesh silica gel
  6. customevaporated

Sources & evidence

ORD record
ord-52971774c512432c825e69c239f92966
Source dataset
uspto-grants-1986_11
Patent number
US04624955

Reaction notes

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