5-Nitro-3-phenyl-1H-indazole → 3-Phenyl-1H-indazol-5-amine

HRID 2183092Notes

Reaction equation

HRID 2183092 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][N:8]=[C:7]2[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)([O-])=O>C(OCC)(=O)C.[Pd]>[NH2:1][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][N:8]=[C:7]2[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

4

Reactant 1

HCID 6174445-Nitro-3-phenyl-1H-indazole

Product 1

HCID 224801043-Phenyl-1H-indazol-5-amineYield 88%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A suspension of 5-nitro-3-phenyl-1H-indazole (0.239 g, 1.0 mmol) and palladium (10 wt % on activated carbon, 30 mg) in ethyl acetate (10 mL) was stirred under hydrogen at ambient temperature for 18 hours. It was filtered with celite and washed with ethyl acetate. The filtrate was concentrated and the residue was then purified by chromatography (SiO2, 30-50% ethyl acetate/hexane) to provide the title compound (0.184 g, 88% yield): mp 104° C.; 1H NMR (CDCl3) δ 10.40 (br s, 1H), 7.94 (d, 2H), 7.51 (m, 2H), 7.20-7.42 (m, 3H), 6.90 (m, 1H), 3.6 (br, 2H); EI-MS (m/z) 209 [M]+.

Workup

  1. filtrationIt was filtered with celite
  2. washwashed with ethyl acetate
  3. concentrationThe filtrate was concentrated
  4. customthe residue was then purified by chromatography (SiO2, 30-50% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-999a1b12f3b34566a403ca0006bb7761
Source dataset
uspto-grants-2005_05
Patent number
US06897231B2

Reaction notes

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