tert-butyl 2-methyl-6-nitro-3-oxo-2,3-dihydro-1H-indazole-1-carboxylate → tert-Butyl 6-amino-2-methyl-3-oxo-2,3-dihydro-1H-indazole-1-carboxylate

HRID 56611Notes

Reaction equation

HRID 56611 reaction equation
[CH3:1][N:2]1[C:10](=[O:11])[C:9]2[C:4](=[CH:5][C:6]([N+:12]([O-])=O)=[CH:7][CH:8]=2)[N:3]1[C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16]>C(O)C.[Pd]>[NH2:12][C:6]1[CH:5]=[C:4]2[C:9]([C:10](=[O:11])[N:2]([CH3:1])[N:3]2[C:15]([O:17][C:18]([CH3:19])([CH3:20])[CH3:21])=[O:16])=[CH:8][CH:7]=1

Participants

4

Reactant 1

HCID 117622641tert-butyl 2-methyl-6-nitro-3-oxo-2,3-dihydro-1H-indazole-1-carboxylate

Product 1

HCID 117622556tert-Butyl 6-amino-2-methyl-3-oxo-2,3-dihydro-1H-indazole-1-carboxylate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 715 mg (2.4 mmol) of tert-butyl 2-methyl-6-nitro-3-oxo-2,3-dihydro-1H-indazole-1-carboxylate in 30 ml of ethanol was hydrogenated in the presence of 52 mg of palladium (10% on activated carbon) at RT and standard pressure. The reaction mixture was then filtered through Celite and the filtrate was concentrated under reduced pressure and dried. Yield: 668 mg (100% of theory)

Workup

  1. filtrationThe reaction mixture was then filtered through Celite
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customdried

Sources & evidence

ORD record
ord-7618e840d8124868880e95a99fdac723
Source dataset
uspto-grants-2016_09
Patent number
US09434690B2

Reaction notes

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