Nitric Acid → HCID 178526903, compound

HRID 1930371Notes

Reaction equation

HRID 1930371 reaction equation
[N+:1]([O-:4])(O)=[O:2].[NH:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH:7]=[N:6]1.C(OC(=O)C)(=O)C>C(O)(=O)C>[N+:1]([C:7]1[C:8]2[C:13](=[CH:12][CH:11]=[CH:10][CH:9]=2)[NH:5][N:6]=1)([O-:4])=[O:2]

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 7918Acetic AnhydrideHCID 92211H-Indazole

Product 1

HCID 178526903HCID 178526903, compoundYield 49%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Nitric acid (2 mL) was added to a stirred solution of indazole (5.0 g, 42 mmol) in acetic acid (40 mL) at 0° C. The resulting mixture was stirred at RT for 30 min. Acetic anhydride (6 mL) was added in one portion and the mixture was stirred at RT overnight. The solvent was removed under reduced pressure and the residue was purified by chromatography to give 3-nitro-1 H-indazole (3.4 g, 49% yield). 1H NMR (400 MHz, DMSO-d4): δ 14.46 (s, 1 H), 8.12 (m, 1 H), 7.76 (m, 1 H), 7.57 (m, 1 H), 7.48 (m, 1 H).

Workup

  1. stirringthe mixture was stirred at RT overnight
  2. customThe solvent was removed under reduced pressure
  3. customthe residue was purified by chromatography

Sources & evidence

ORD record
ord-1c8c5ff50e3c4640afe7caac7691d877
Source dataset
uspto-grants-2012_05
Patent number
US08188113B2

Reaction notes

Loading…