Hydrochloric Acid → 4-bromo-1H-indazole

HRID 2403346Notes

Reaction equation

HRID 2403346 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[N:5][N:6]2C(=O)C.Cl>CO>[Br:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[N:5][NH:6]2

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 454801851-Acetyl-4-bromo-1H-indazole

Product 1

HCID 223525484-bromo-1H-indazoleYield 93%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of the 1-(4-bromo-indazol-1-yl)-ethanone (3.09 g, 12.9 mmol) in MeOH (50 mL) was added 6N aqueous HCl (30 mL) and the mixture was stirred at room temperature for 7 h. The MeOH was evaporated and the mixture partitioned between EtOAc (2×50 mL) and water (50 mL). The combined organic layers were washed with brine (50 mL), separated and dried (MgSO4). The solvent was removed by evaporation under reduced pressure to give 4-bromo-1H-indazole (2.36 g, 93%).

Workup

  1. customThe MeOH was evaporated
  2. customthe mixture partitioned between EtOAc (2×50 mL) and water (50 mL)
  3. washThe combined organic layers were washed with brine (50 mL)
  4. customseparated
  5. dry with materialdried (MgSO4)
  6. customThe solvent was removed by evaporation under reduced pressure

Sources & evidence

ORD record
ord-d4f8dbe52afb4101a12fea6e765e35db
Source dataset
uspto-grants-2014_08
Patent number
US08802670B2

Reaction notes

Loading…