Sodium Nitrite → 1H-Indazole, 6-broMo-5-chloro-

HRID 2203219Notes

Reaction equation

HRID 2203219 reaction equation
[Br:1][C:2]1[C:3]([Cl:10])=[CH:4][C:5]([CH3:9])=[C:6]([CH:8]=1)[NH2:7].[N:11]([O-])=O.[Na+]>C(O)(=O)C.O>[Br:1][C:2]1[CH:8]=[C:6]2[C:5]([CH:9]=[N:11][NH:7]2)=[CH:4][C:3]=1[Cl:10]

Participants

5

Reactant 2

HCID 23668193Sodium NitriteHCID 467382955-Bromo-4-chloro-2-methylaniline

Product 1

HCID 748904621H-Indazole, 6-broMo-5-chloro-Yield 64%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

To 5-bromo-4-chloro-2-methylaniline (1 g, 4.54 mmol) in acetic acid (10 mL) was added a solution of sodium nitrite (0.329 g, 4.76 mmol) in water (1 mL). The mixture was heated at reflux for 2 hours and was subsequently cooled and concentrated. The residue was partitioned in water and extracted with EtOAc. The combined organic layers were washed with brine, dried over magnesium sulfate, and concentrated to give the title compound as a red-brown solid (0.67 g, 64%). ESI-MS m/z [M+H]+ 232.2.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 2 hours
  3. temperaturewas subsequently cooled
  4. concentrationconcentrated
  5. customThe residue was partitioned in water
  6. extractionextracted with EtOAc
  7. washThe combined organic layers were washed with brine
  8. dry with materialdried over magnesium sulfate
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-b4940dc236604863af7af5a7ea80f67f
Source dataset
uspto-grants-2016_06
Patent number
US09365566B2

Reaction notes

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