Ammonia → 4-Nitroindazole

HRID 1175746Notes

Reaction equation

HRID 1175746 reaction equation
[CH3:1][C:2]1[C:8]([N+:9]([O-:11])=[O:10])=[CH:7][CH:6]=[CH:5][C:3]=1[NH2:4].[N:12]([O-])=O.[Na+].O.N>C(O)(=O)C>[N+:9]([C:8]1[CH:7]=[CH:6][CH:5]=[C:3]2[C:2]=1[CH:1]=[N:12][NH:4]2)([O-:11])=[O:10]

Participants

6

Reactant 4

HCID 222AmmoniaHCID 962WaterHCID 117832-Methyl-3-nitroanilineHCID 23668193Sodium Nitrite

Product 1

HCID 180574-Nitroindazole

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 2-methyl-3-nitro aniline (1 mmol) in acetic acid was stirred at room temperature and sodium nitrite (1.1 mmol) was added to the reaction mixture. Reaction mixture was stirred at room temperature for 5 hours. Reaction mixture was poured into water and neutralized with ammonia. Product precipitated out, was filtered and washed with water. It was then purified by column chromatography to afford the desired compound as a pale yellow solid.

Workup

  1. customReaction mixture
  2. customReaction mixture
  3. customProduct precipitated out
  4. filtrationwas filtered
  5. washwashed with water
  6. customIt was then purified by column chromatography

Sources & evidence

ORD record
ord-8f7b356f42f14c6fb351efe7c9f84c50
Source dataset
uspto-grants-2010_11
Patent number
US07842703B2

Reaction notes

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