2,6-dinitro-2H-indazole → 3-Methoxy-6-nitro-1H-indazole

HRID 388929Notes

Reaction equation

HRID 388929 reaction equation
[N+]([N:4]1[CH:12]=[C:11]2[C:6]([CH:7]=[C:8]([N+:13]([O-:15])=[O:14])[CH:9]=[CH:10]2)=[N:5]1)([O-])=O.[CH3:16][O-:17].[Na+]>C1COCC1.C(OCC)(=O)C>[CH3:16][O:17][C:12]1[C:11]2[C:6](=[CH:7][C:8]([N+:13]([O-:15])=[O:14])=[CH:9][CH:10]=2)[NH:5][N:4]=1

Participants

5

Reactant 2

HCID 3308402,6-dinitro-2H-indazoleHCID 10942334Sodium Methoxide

Product 1

HCID 684434923-Methoxy-6-nitro-1H-indazole

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2,6-dinitro-2H-indazole (1 mmol) (prepared by nitration of 6-nitroindazole; Wrzeciono, et al., E. Pharmazie, 1980, 35, 593-596) in dry THF (4 mL) at 0° C., solid sodium methoxide (4 mmol) was added in portions. The reaction mixture was allowed to warm to room temperature and stirred for 12 h. The contents were diluted with ethyl acetate (20 mL), washed with water (2×10 mL) and brine (10 mL) and dried over anhydrous sodium sulfate. The solvent was removed in vacuo to yield 3-methoxy-6-nitro-1H-indazole as a brown solid, which was reduced to 3-methoxy-1H-indazol-6-ylamine by hydrogenation following general procedure F.

Workup

  1. washwashed with water (2×10 mL) and brine (10 mL)
  2. dry with materialdried over anhydrous sodium sulfate
  3. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-10e633b8f35b4c759ee7e33299835e06
Source dataset
uspto-grants-2013_02
Patent number
US08377983B2

Reaction notes

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