1,2-Dihydro-5-nitro-1-(phenylmethyl)-3H-indazol-3-one → HCID 68730847, compound

HRID 490552Notes

Reaction equation

HRID 490552 reaction equation
[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([N+:17]([O-])=O)=[CH:14][CH:15]=2)[C:10](=[O:20])[NH:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>CO.[Pd]>[NH2:17][C:13]1[CH:12]=[C:11]2[C:16](=[CH:15][CH:14]=1)[N:8]([CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[NH:9][C:10]2=[O:20]

Participants

4

Reactant 1

HCID 3849951,2-Dihydro-5-nitro-1-(phenylmethyl)-3H-indazol-3-one

Product 1

HCID 68730847HCID 68730847, compoundYield 99.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 1-benzyl-5-nitro-1,2-dihydro-indazol-3-one (0.44 g) in MeOH (50 mL) was added Pd/C(10%) catalyst (0.1 g) and the reaction mixture was stirred for four hours at ambient temperature under a hydrogen atmosphere using a balloon. After this time the reaction mixture was filtered through Celite® which was washed with more EtOAc. The combined organic solution was evaporated in vacuo for afford the desired 5-amino-1-benzyl-1,2-dihydro-indazol-3-one (0.39 g) which was taken into the next reaction without further purification. MS (ESI+): 240.1 ([M+H]+).

Workup

  1. filtrationAfter this time the reaction mixture was filtered through Celite® which
  2. washwas washed with more EtOAc
  3. customThe combined organic solution was evaporated in vacuo

Sources & evidence

ORD record
ord-a94f0d8804e84c1ca686bc7032f4d9e9
Source dataset
uspto-grants-2009_05
Patent number
US07528158B2

Reaction notes

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