Hydrazine → 5-bromo-1H-indazole

HRID 2307781Notes

Reaction equation

HRID 2307781 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5](F)=[C:6]([CH:9]=1)[CH:7]=O.[NH2:11][NH2:12]>>[Br:1][C:2]1[CH:9]=[C:6]2[C:5](=[CH:4][CH:3]=1)[NH:12][N:11]=[CH:7]2

Participants

3

Reactant 2

HCID 9321HydrazineHCID 7363275-Bromo-2-fluorobenzaldehyde

Product 1

HCID 7619295-bromo-1H-indazoleYield 38%

Procedure

A mixture of 5-bromo-2-fluorobenzaldehyde (10 g, 49.2 mmol) and 98% hydrazine (20 mL) was heated to reflux for 5 hours, poured over ice, and filtered. The solid was recrystallized from H2O/methanol to provide the desired product (3.7 g, 38%).

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 5 hours
  3. additionpoured over ice
  4. filtrationfiltered
  5. customThe solid was recrystallized from H2O/methanol

Sources & evidence

ORD record
ord-3f26d9c455a940d0aeab8cc6b9bcc823
Source dataset
uspto-grants-2004_12
Patent number
US06831175B2

Reaction notes

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