Water → HCID 13749205, compound

HRID 1732010Notes

Reaction equation

HRID 1732010 reaction equation
Cl[C:2]1[C:7]([C:8](=[O:17])[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[O:15][CH3:16])=[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]=[CH:11][C:10]=3[O:15][CH3:16])[C:3]=2[CH:20]=[N:19]1)[CH3:22]

Participants

6

Reactant 4

HCID 962WaterHCID 443297Hydroxyamine hydrochlorideHCID 521998p-Toluenesulfonic acid monohydrateHCID 14171321HCID 14171321, compound

Product 1

HCID 13749205HCID 13749205, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Five grams of 4-chloro-1-ethyl-5-(2-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 2.95 g of product, mp 126°-127° C. The melting point was unchanged after recrystallization from ethyl acetate/pentane.

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-79746f5efa614c3aae391a796f678582
Source dataset
uspto-grants-1986_11
Patent number
US04624955

Reaction notes

Loading…