N-(1-acetyl-5-nitro-1H-indazol-3-yl)acetamide → N-(1-acetyl-5-amino-1H-indazol-3-yl)acetamide

HRID 227696Notes

Reaction equation

HRID 227696 reaction equation
[C:1]([N:4]1[C:12]2[C:7](=[CH:8][C:9]([N+:13]([O-])=O)=[CH:10][CH:11]=2)[C:6]([NH:16][C:17](=[O:19])[CH3:18])=[N:5]1)(=[O:3])[CH3:2]>CO.[Pd]>[C:1]([N:4]1[C:12]2[C:7](=[CH:8][C:9]([NH2:13])=[CH:10][CH:11]=2)[C:6]([NH:16][C:17](=[O:19])[CH3:18])=[N:5]1)(=[O:3])[CH3:2]

Participants

4

Reactant 1

HCID 57755833N-(1-acetyl-5-nitro-1H-indazol-3-yl)acetamide

Product 1

HCID 57755866N-(1-acetyl-5-amino-1H-indazol-3-yl)acetamideYield 98%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

The product from Step (b) above (3.0 g, 11.4 mmol) and 5% Pd/C (1 g) were combined in MeOH (40 mL) and hydrogenated uner a balloon of H2 for 3 h. The mixture was filtered through Celite and the filtrate was concentrated to give the title compound as a dark solid (2.6 g, 98%). NMR 1H NMR (400 MHz, DMSO-D6) δ 10.62 (s, 1H), 7.97 (dd, J=7.9, 1.8, 1H), 6.93-6.89 (m, 2H), 5.26 (s, 2H), 2.52 (s, 3H), 2.08 (s, 3H) (MS m/z 233.2 [M+H]+

Workup

  1. filtrationThe mixture was filtered through Celite
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-3fa5aba120e84866967b923e5c38957f
Source dataset
uspto-grants-2009_07
Patent number
US07560467B2

Reaction notes

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