Ethanol → 2-Amino-4-bromo-5-methylbenzoic acid
Reaction equation
[NH2:1][C:2]1[CH:9]=[C:8]([Br:10])[C:7]([CH3:11])=[CH:6]C=1C#N.[OH-:12].[Na+].[CH3:14][CH2:15][OH:16]>>[NH2:1][C:2]1[CH:9]=[C:8]([Br:10])[C:7]([CH3:11])=[CH:6][C:14]=1[C:15]([OH:12])=[O:16]Participants
4
Procedure
A mixture of 2-amino-4-bromo-5-methylbenzonitrile (2.95 g, 14.0 mmol) in a mixture of EtOH (21 mL) and 2 M aqueous NaOH (34.9 mL, 69.9 mmol) was heated at reflux overnight. After cooling to room temperature, the ethanol was removed under reduced pressure, and the aqueous residue was diluted with water. After adjustment of the pH to about 5 with concentrated aqueous HCl, the mixture was stirred for 30 min and the precipitate was collected by filtration and washed with water. The resulting wet solid was dissolved in EtOAc, washed with brine, dried and concentrated to provide 2-amino-4-bromo-5-methylbenzoic acid as a pale yellow solid (2.92 g, 91% yield). Mass spectrum m/z 212, 214 (M+H)+.
Workup
- temperaturewas heated
- temperatureat reflux overnight
- customthe ethanol was removed under reduced pressure
- additionthe aqueous residue was diluted with water
- filtrationthe precipitate was collected by filtration
- washwashed with water
- dissolutionThe resulting wet solid was dissolved in EtOAc
- washwashed with brine
- customdried
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-a7d53b41fa4042f78c3f2b0b62fc3eb6
- Source dataset
- uspto-grants-2016_05
- Patent number
- US09334290B2
Reaction notes
Loading…