Hydrazine → HCID 178434225, compound

HRID 643344Notes

Reaction equation

HRID 643344 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5](F)=[C:6]([C:8](=O)[CH3:9])[CH:7]=1.[NH2:12][NH2:13]>>[Br:1][C:2]1[CH:7]=[C:6]2[C:5](=[CH:4][CH:3]=1)[NH:13][N:12]=[C:8]2[CH3:9]

Participants

3

Reactant 2

HCID 9321HydrazineHCID 226074761-(5-Bromo-2-fluorophenyl)ethanone

Product 1

HCID 178434225HCID 178434225, compoundYield 92.5%

Procedure

To 1-(5-Bromo-2-fluoro-phenyl)-ethanone 103 (95.7 g, 0.441 mol) was added anhydrous hydrazine (240 mL, 7.65 mol). The reaction mixture was heated under reflux for 10 hours. The reaction mixture was allowed to cool to room temperature and was stirred for 16 hours. The reaction mixture was added to ice (1.4 L). The reaction mixture was stirred for 30 minutes. The reaction mixture was filtered and the white solid product was washed with water. The white solid was dried in a vacuum oven to afford the desired 5-bromo-3-methyl-1H-indazole 104 (86.1 g, 0.408 mol) which was used without further purification.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureunder reflux for 10 hours
  3. stirringThe reaction mixture was stirred for 30 minutes
  4. filtrationThe reaction mixture was filtered
  5. washthe white solid product was washed with water
  6. customThe white solid was dried in a vacuum oven

Sources & evidence

ORD record
ord-cb200187ed3a4715be6b05d185e3c66a
Source dataset
uspto-grants-2010_04
Patent number
US07700601B2

Reaction notes

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