HCID 18616782, compound → HCID 18616705, compound

HRID 1264035Notes

Reaction equation

HRID 1264035 reaction equation
[N+:1]([C:4]1[CH:12]=[C:11]2[C:7]([C:8]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)=[N:9][NH:10]2)=[CH:6][CH:5]=1)([O-])=O>[H][H].[Pd]>[C:13]1([C:8]2[C:7]3[C:11](=[CH:12][C:4]([NH2:1])=[CH:5][CH:6]=3)[NH:10][N:9]=2)[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

3

Reactant 1

HCID 18616782HCID 18616782, compound

Product 1

HCID 18616705HCID 18616705, compoundYield 71.5%

Reagents, catalysts & solvents 1

HCID 178506449HCID 178506449, compoundCatalyst

Procedure

To a solution of 2-chloro-5-nitro-benzophenone (1.0 g) in THF (tetrahydrofuran) (15 ml) was added anhydrous hydrazine (120 mg). The resulting reaction mixture was kept stirring at room temperature for 2-4 hours. The solvent was removed in vacuo and the residue dissolved in EtOAc, washed with water and brine, dried over Na2SO4. Removal of the solvent afforded (0.8 g, 88%) product 6-Nitro-3-phenyl-1H-indazole (5). 6-Nitro-3-phenyl-1H-indazole was hydrogenated over H2/Pd and gave 0.5 g of 3-phenyl-1H-indazol-6-ylamine (71.5%). M/z: 210.0. 1H NMR (CD3OD): 7.86 (d, 2H, J=7.9 Hz), 7.47 (t, J=8.1 Hz), 7.35 (t, 3H, J=8.7 Hz), 7.01 (d, 1H, J=8.7 Hz).

Sources & evidence

ORD record
ord-a26a5e9dfa4f47e7a9624c5a738aed2e
Source dataset
uspto-grants-2003_04
Patent number
US06541481B2

Reaction notes

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