Ethyl Acetate → 1-(4-methoxybenzyl)-1H-indazol-4-amine

HRID 2237410Notes

Reaction equation

HRID 2237410 reaction equation
[CH3:1][O:2][C:3]1[CH:21]=[CH:20][C:6]([CH2:7][N:8]2[C:16]3[C:11](=[C:12]([N+:17]([O-])=O)[CH:13]=[CH:14][CH:15]=3)[CH:10]=[N:9]2)=[CH:5][CH:4]=1.C(OCC)(=O)C>C(O)C.[Pt](=O)=O>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:7][N:8]2[C:16]3[CH:15]=[CH:14][CH:13]=[C:12]([NH2:17])[C:11]=3[CH:10]=[N:9]2)=[CH:20][CH:21]=1

Participants

5

Reactant 2

HCID 8857Ethyl AcetateHCID 685820841-(4-methoxybenzyl)-4-nitro-1H-indazole

Product 1

HCID 685830011-(4-methoxybenzyl)-1H-indazol-4-amineYield 100%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 702EthanolSolvent

Procedure

A suspension of 1-(4-methoxybenzyl)-4-nitro-1H-indazole (9 g, 31.77 mmol) and platinum(IV) oxide (0.433 g, 1.91 mmol) in ethanol (150 mL)/ethyl acetate (10 mL) was hydrogenated under 40 psi at 25° C. for 2 hours. The resulting mixture was filtered and the filtrate was concentrated to dryness to afford 1-(4-methoxybenzyl)-1H-indazol-4-amine (8.03 g, 100%) as a yellow-orange solid. Mass spectrum: MH+ 254.

Workup

  1. filtrationThe resulting mixture was filtered
  2. concentrationthe filtrate was concentrated to dryness

Sources & evidence

ORD record
ord-f012f317e32a4e4baf04b166e474b40f
Source dataset
uspto-grants-2010_05
Patent number
US07718653B2

Reaction notes

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