Sodium Hydroxide → 2-fluoro-3-(N-methylbenzamido)benzoic acid
Reaction equation
[OH-].[Na+].[F:3][C:4]1[C:13]([N:14]([CH3:23])[C:15](=[O:22])[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[CH:12][CH:11]=[CH:10][C:5]=1[C:6]([O:8]C)=[O:7]>CO>[F:3][C:4]1[C:13]([N:14]([CH3:23])[C:15](=[O:22])[C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)=[CH:12][CH:11]=[CH:10][C:5]=1[C:6]([OH:8])=[O:7]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 60 °C
Procedure
Sodium hydroxide (0.26 g, 6.50 mmol) was dissolved in methanol (30 ml), and methyl 2-fluoro-3-(N-methylbenzamido)benzoate (1.42 g, 4.94 mmol) was added thereto. The mixture was heated for 3 hours at 60° C. The mixture was cooled to room temperature, and then the solvent was concentrated under reduced pressure. The concentration residue was dissolved in water, and washed with methylene chloride. While the aqueous layer was cooled, the pH thereof was adjusted to 2 to 3 with a 1N hydrochloric acid, and a solid precipitated during continued agitation. The resultant solid was filtered, washed with water, and dried at 50° C., as a result of which 1.25 g (yield: 94%) of the indicated compound was obtained.
Workup
- temperatureThe mixture was cooled to room temperature
- concentrationthe solvent was concentrated under reduced pressure
- dissolutionThe concentration residue was dissolved in water
- washwashed with methylene chloride
- temperatureWhile the aqueous layer was cooled
- customa solid precipitated during continued agitation
- filtrationThe resultant solid was filtered
- washwashed with water
- customdried at 50° C.
Sources & evidence
- ORD record
- ord-49f6b273216541ae9be31ac57d4e4232
- Source dataset
- uspto-grants-2014_10
- Patent number
- US08853440B2
Reaction notes
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