Water → 5-Nitro-3-phenyl-1H-indazole

HRID 896839

Reaction equation

HRID 896839 reaction equation
Cl[C:2]1[CH:15]=[CH:14][C:13]([N+:16]([O-:18])=[O:17])=[CH:12][C:3]=1[C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=O.O.[NH2:20][NH2:21].O>C(O)C>[N+:16]([C:13]1[CH:12]=[C:3]2[C:2](=[CH:15][CH:14]=1)[NH:21][N:20]=[C:4]2[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)([O-:18])=[O:17]

Participants

5

Reactant 3

HCID 962WaterHCID 24654Hydrazine hydrate (1:1)HCID 1185912-Chloro-5-nitrobenzophenone

Product 1

HCID 6174445-Nitro-3-phenyl-1H-indazoleYield 96.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 2-chloro-5-nitrobenzophenone (15 g, 57 mmol) in ethanol (300 mL) was added hydrazine monohydrate (50 mL, 1 mol). The resultant solution was stirred overnight (16 hrs.) at ambient temperature, then poured into water (2 L) and stirred for an additional 2 hours. The precipitate that formed was collected by filtration, washed with water (2×100 mL) and air dried to give 5-Nitro-3-phenyl-1H-indazole 11a (13.1 g, 80%) as a yellow solid: 1H NMR (DMSO-d6) δ 7.48 (tt, 1H, J=1.3, 7.4 Hz), 7.58 (dd, 2H, J=7.1, 7.4 Hz), 7.78 (d, 1H, J=9.2 Hz), 8.01 (dd, 2H, J=1.3, 7.1 Hz), 8.25 (dd, 1H, J=2.1, 9.2 Hz), 8.91 (d, 1H, J=2.1 Hz), 13.88 (s, 1H). Anal. (C13H9N3O2) C, H, N.

Workup

  1. customThe precipitate that formed
  2. filtrationwas collected by filtration
  3. washwashed with water (2×100 mL) and air
  4. customdried

Sources & evidence

ORD record
ord-94ff5284e69c4c4d9cdeddf9e947f79b
Source dataset
uspto-grants-2005_07
Patent number
US06919461B2

Linked notes

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