Water → HCID 13749202, compound

HRID 1732007Notes

Reaction equation

HRID 1732007 reaction equation
Cl[C:2]1[C:7]([C:8](=[O:16])[C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([CH3:15])[CH:10]=2)=[CH:6][N:5]=[C:4]2[N:17]([CH2:20][CH3:21])[N:18]=[CH:19][C:3]=12.Cl.[NH2:23]O.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.O>C(O)(=O)C.ClCCl>[CH2:20]([N:17]1[C:4]2[N:5]=[CH:6][C:7]3[C:2](=[N:23][O:16][C:8]=3[C:9]3[CH:10]=[C:11]([CH3:15])[CH:12]=[CH:13][CH:14]=3)[C:3]=2[CH:19]=[N:18]1)[CH3:21]

Participants

7

Reactant 4

HCID 962WaterHCID 443297Hydroxyamine hydrochlorideHCID 521998p-Toluenesulfonic acid monohydrateHCID 14171319HCID 14171319, compound

Product 1

HCID 13749202HCID 13749202, compoundYield 75.4%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6344DichloromethaneSolvent

Procedure

4-Chloro-1-ethyl-5-(3-methylbenzoyl)-1H-pyrazolo[3,4-b]pyridine (2.0 g) and hydroxylamine hydrochloride (6.0 g) were suspended in 200 ml of acetic acid, and to this was added 0.5 g of p-toluenesulfonic acid monohydrate. The reaction mixture was refluxed for 2 hours and then distributed between water and 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, eluting with 10% ethyl acetate/dichloromethane. By combining the appropriate fractions, 1.40 g of product was obtained, mp 178°-179°. This product was combined with the product of another run and recrystallized from ethyl acetate to give product of mp 180°-181° C.

Workup

  1. temperatureThe reaction mixture was refluxed for 2 hours
  2. washThe organic phase was washed four times with water
  3. customIt was then evaporated
  4. customchromatographed over 230-400 mesh silica gel
  5. washeluting with 10% ethyl acetate/dichloromethane

Sources & evidence

ORD record
ord-64142854f6f14c04bf3f8a997dcb2b66
Source dataset
uspto-grants-1986_11
Patent number
US04624955

Reaction notes

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