Water → HCID 13749204, compound

HRID 1732009Notes

Reaction equation

HRID 1732009 reaction equation
Cl[C:2]1[C:7]([C:8](=[O:19])[C:9]2[CH:14]=[CH:13][C:12]([C:15]([F:18])([F:17])[F:16])=[CH:11][CH:10]=2)=[CH:6][N:5]=[C:4]2[N:20]([CH2:23][CH3:24])[N:21]=[CH:22][C:3]=12.Cl.[NH2:26]O.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.O>C(O)(=O)C>[CH2:23]([N:20]1[C:4]2[N:5]=[CH:6][C:7]3[C:2](=[N:26][O:19][C:8]=3[C:9]3[CH:10]=[CH:11][C:12]([C:15]([F:17])([F:18])[F:16])=[CH:13][CH:14]=3)[C:3]=2[CH:22]=[N:21]1)[CH3:24]

Participants

6

Reactant 4

HCID 962WaterHCID 443297Hydroxyamine hydrochlorideHCID 521998p-Toluenesulfonic acid monohydrateHCID 20226393HCID 20226393, compound

Product 1

HCID 13749204HCID 13749204, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

4-Chloro-1-ethyl-5-(4-trifluoromethylbenzoyl)-1H-pyrazolo[3,4-b]pyridine (3.10 g) was refluxed for 2 hours in 300 ml of acetic acid containing 9 g of hydroxylamine hydrochloride and 0.6 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 purified by chromatography over 230-400 mesh silica gel (10% ethyl acetate/dichloromethane). In this way, 2.15 g of product was obtained, mp 243°-245°. Recrystallization from ethyl acetate gave analytically pure product, mp 244°-245° C.

Workup

  1. extractionextracted with dichloromethane
  2. washThe organic phase was washed well with water
  3. customdried
  4. customevaporated
  5. custompurified by chromatography over 230-400 mesh silica gel (10% ethyl acetate/dichloromethane)

Sources & evidence

ORD record
ord-0ac3bb5e2c654235b3c8f8aaac3ba647
Source dataset
uspto-grants-1986_11
Patent number
US04624955

Reaction notes

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