Hydrochloric Acid → HCID 13749201, compound

HRID 1732006Notes

Reaction equation

HRID 1732006 reaction equation
Cl[C:2]1[C:7]([C:8](=[O:16])[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[CH3:15])=[CH:6][N:5]=[C:4]2[N:17]([CH2:20][CH3:21])[N:18]=[CH:19][C:3]=12.Cl.Cl.[NH2:24]O.O>C(O)(=O)C>[CH2:20]([N:17]1[C:4]2[N:5]=[CH:6][C:7]3[C:2](=[N:24][O:16][C:8]=3[C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=3[CH3:15])[C:3]=2[CH:19]=[N:18]1)[CH3:21]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 443297Hydroxyamine hydrochlorideHCID 14171318HCID 14171318, compound

Product 1

HCID 13749201HCID 13749201, compoundYield 44.1%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

4-Chloro-1-ethyl-5-(2-methylbenzoyl)-1H-pyrazolo[3,4-b]pyridine (5.40 g) was refluxed for 2 hours in 300 ml of glacial acetic acid containing 10 ml of concentrated hydrochloric acid and 10 g of hydroxylamine hydrochloride. At the end of this time the reaction mixture was poured into water and extracted with dichloromethane. The organic phase was washed four times with water and once with saturated sodium bicarbonate solution. It was then evaporated and chromatographed over 230-400 mesh silica gel (10% ethyl acetate/dichloromethane) to give 2.21 g of product, mp 168°-170°. This product was recrystallized from ethyl acetate together with the product of another run to give analytically pure material, mp 170°-171° C.

Workup

  1. extractionextracted with dichloromethane
  2. washThe organic phase was washed four times with water
  3. customIt was then evaporated
  4. customchromatographed over 230-400 mesh silica gel (10% ethyl acetate/dichloromethane)

Sources & evidence

ORD record
ord-f55c939cb32842ef99c37dee78c065b3
Source dataset
uspto-grants-1986_11
Patent number
US04624955

Reaction notes

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