HCID 18998521, compound → HCID 21846513, compound

HRID 2260571Notes

Reaction equation

HRID 2260571 reaction equation
[N:1]([C:4]1[CH:9]=[CH:8][N:7]=[C:6]2[N:10](CC3C=CC=CC=3)[N:11]=[CH:12][C:5]=12)=[N+]=[N-].[ClH:20].CO.[H][H]>CO.[C+4].[OH-].[Pd+2].[OH-].[OH-].[OH-].[OH-].[OH-]>[ClH:20].[ClH:20].[NH2:1][C:4]1[CH:9]=[CH:8][N:7]=[C:6]2[NH:10][N:11]=[CH:12][C:5]=12

Participants

6

Reactant 3

HCID 18998521HCID 18998521, compoundHCID 21893726Hydrochloride methanolHCID 178418361HCID 178418361, compound

Product 1

HCID 21846513HCID 21846513, compound

Reagents, catalysts & solvents 2

HCID 178420936HCID 178420936, compoundCatalystHCID 887MethanolSolvent

Procedure

A solution (40 ml) of 4-azido-1-benzyl-1H-pyrazolo[3,4-b]pyridine (2.7 g), 10% palladium hydroxide carbon (1.0 g) and 15% hydrochloric acid-methanol (1 ml) in methanol was stirred in an autoclave at initial hydrogen pressure of 10 atm and at 40°-50° C. for 5 hours. After completion of the reaction, the catalyst was filtered off and the filtrate was concentrated under reduced pressure to give crystals. Recrystallization from methanol-ethyl acetate gave 1.9 g of 4-amino-1H-pyrazolo[3,4-b]pyridine dihydrochloride.

Workup

  1. customAfter completion of the reaction
  2. filtrationthe catalyst was filtered off
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customto give crystals
  5. customRecrystallization from methanol-ethyl acetate

Sources & evidence

ORD record
ord-10a3ca6c8009498fbeea4a451e0a1d41
Source dataset
uspto-grants-1995_12
Patent number
US05478838

Reaction notes

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