Water → HCID 13749195, compound

HRID 1732001Notes

Reaction equation

HRID 1732001 reaction equation
[C:1]([C:4]1[C:5](Cl)=[C:6]2[CH:12]=[N:11][N:10]([CH2:13][CH3:14])[C:7]2=[N:8][CH:9]=1)(=[O:3])[CH3:2].Cl.[NH2:17]O.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.O>C(O)(=O)C>[CH2:13]([N:10]1[C:7]2[N:8]=[CH:9][C:4]3[C:5](=[N:17][O:3][C:1]=3[CH3:2])[C:6]=2[CH:12]=[N:11]1)[CH3:14]

Participants

6

Reactant 4

HCID 962WaterHCID 443297Hydroxyamine hydrochlorideHCID 521998p-Toluenesulfonic acid monohydrateHCID 12281137HCID 12281137, compound

Product 1

HCID 13749195HCID 13749195, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

5-Acetyl-4-chloro-1-ethyl-1H-pyrazolo[3,4-b]pyridine (4.60 g) was refluxed for 2 hours in 450 ml of glacial acetic acid containing 15 g of hydroxylamine hydrochloride and 1.0 g of p-toluenesulfonic acid monohydrate. At the end of this time the reaction volume was reduced to ca. 200 ml under reduced pressure and then it was poured into 800 ml of water. The amorphous precipitate was filtered off and purified over 230-400 mesh silica gel (5% ethyl acetate/dichloromethane). The appropriate fractions were combined and evaporated and the resultant crystalline product was washed with pentane to give 1.75 g, mp 181°-182° C.

Workup

  1. filtrationThe amorphous precipitate was filtered off
  2. custompurified over 230-400 mesh silica gel (5% ethyl acetate/dichloromethane)
  3. customevaporated
  4. washthe resultant crystalline product was washed with pentane
  5. customto give 1.75 g, mp 181°-182° C.

Sources & evidence

ORD record
ord-a2cf964c84ab4edaada1218c38554383
Source dataset
uspto-grants-1986_11
Patent number
US04624955

Reaction notes

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