1-Benzyl-5-nitro-1H-indazole → 1-(Phenylmethyl)-1H-indazol-5-amine

HRID 1815912Notes

Reaction equation

HRID 1815912 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)[CH:10]=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>CO.CCOC(C)=O.[Pd]>[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([NH2:17])=[CH:14][CH:15]=2)[CH:10]=[N:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 1

HCID 219520821-Benzyl-5-nitro-1H-indazole

Product 1

HCID 2120691-(Phenylmethyl)-1H-indazol-5-amine

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To 906.4 mg (3.58 mmol) of 1-benzyl-5-nitro-1H-indazole (Step 1) in 20 mL of MeOH and 5 mL of EtOAc at RT was added a slurry of 150 mg of 10% Pd—C in 5 mL of MeOH. The resulting slurry was then stirred under a balloon of H2 for 1.2 h, filtered through Celite®, and rinsed with MeOH and EtOAc. Concentration of the filtrate gave (1-benzyl-1H-indazol-5-yl)amine as a pinkish solid: MS m/z=224 [M+H]+. Calc'd for C14H13N3: 223.11.

Workup

  1. filtrationfiltered through Celite®
  2. washrinsed with MeOH and EtOAc

Sources & evidence

ORD record
ord-3e0a080a6514486c8e26be7022d57a94
Source dataset
uspto-grants-2005_04
Patent number
US06881737B2

Reaction notes

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