Ammonium formate → 1-(5-hydroxy-1H-indazol-1-yl)-Ethanone

HRID 1726092Notes

Reaction equation

HRID 1726092 reaction equation
C([O:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[N:14]([C:18](=[O:20])[CH3:19])[N:13]=[CH:12]2)C1C=CC=CC=1.C([O-])=O.[NH4+]>C(O)C.[Pd]>[OH:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[N:14]([C:18](=[O:20])[CH3:19])[N:13]=[CH:12]2

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 225672491-(5-(Benzyloxy)-1H-indazol-1-yl)ethan-1-one

Product 1

HCID 225670481-(5-hydroxy-1H-indazol-1-yl)-EthanoneYield 60.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A suspension of 1 g of 1-(5-benzyloxyindazol-1-yl)ethanone, 1.42 g of ammonium formate and 0.59 g of palladium-on-charcoal at 10% in ethanol is refluxed for 16 hours. After returning to 20° C., the reaction mixture is filtered through a bed of celite and the filtrate is evaporated under reduced pressure. The crude compound thus obtained is triturated in 10 ml of diisopropyl ether and then filtered and dried under reduced pressure to obtain 400 mg of 1-(5-hydroxy-indazol-1-yl)-ethanone, which is characterized.

Workup

  1. temperatureis refluxed for 16 hours
  2. customAfter returning to 20° C.
  3. filtrationthe reaction mixture is filtered through a bed of celite
  4. customthe filtrate is evaporated under reduced pressure
  5. customThe crude compound thus obtained
  6. customis triturated in 10 ml of diisopropyl ether
  7. filtrationfiltered
  8. customdried under reduced pressure

Sources & evidence

ORD record
ord-5898f2d550ea46098ff5ee1536df1bff
Source dataset
uspto-grants-2009_02
Patent number
US07491710B2

Reaction notes

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