Hydrochloric Acid → 4-Bromo-5-fluoro-2-hydrazinylbenzoic acid hydrochloride
Reaction equation
[Br:1][C:2]1[C:10]([F:11])=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[C:4](F)[CH:3]=1.[NH2:13][NH2:14].[ClH:15]>CN1CCCC1=O>[ClH:15].[Br:1][C:2]1[C:10]([F:11])=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[C:4]([NH:13][NH2:14])[CH:3]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 95 °C
Procedure
A mixture of 4-bromo-2,5-difluorobenzoic acid (2.50 g, 10.6 mmol) and hydrazine (3.81 mL, 121 mmol) in N-methyl-2-pyrrolidinone (2 mL) was heated at 95° C. for 4 h. The cooled mixture was poured into vigorously stirred 6 M aqueous HCl (400 mL) which was cooled in an NaCl-ice bath. The resulting precipitate was collected by filtration, washed with 6 M aqueous HCl (200 mL) and dried under vacuum to give 4-bromo-5-fluoro-2-hydrazinylbenzoic acid hydrochloride as a yellow solid (1.88 g, 71% purity, 44% yield), used without further purification.
Workup
- temperaturewas cooled in an NaCl-ice bath
- filtrationThe resulting precipitate was collected by filtration
- washwashed with 6 M aqueous HCl (200 mL)
- customdried under vacuum
Sources & evidence
- ORD record
- ord-7d586237e60148f69ccfc0d9b881c500
- Source dataset
- uspto-grants-2016_05
- Patent number
- US09334290B2
Reaction notes
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