Sodium Hydroxide → 3-chloro-4-fluoro-N-(3-hydroxy-4-methyl-phenyl)-benzamide
Reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:26]=[CH:27][C:28]=1[F:29])[C:5]([NH:7][C:8]1[CH:9]=[CH:10][C:11]([CH3:25])=[C:12]([O:14]C(=O)C2C=CC(F)=C(Cl)C=2)[CH:13]=1)=[O:6].[OH-].[Na+]>O1CCCC1.CO>[Cl:1][C:2]1[CH:3]=[C:4]([CH:26]=[CH:27][C:28]=1[F:29])[C:5]([NH:7][C:8]1[CH:9]=[CH:10][C:11]([CH3:25])=[C:12]([OH:14])[CH:13]=1)=[O:6]Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Procedure
3-Chloro-4-fluoro-benzoic acid 5-(3-chloro-4-fluoro-benzoylamino)-2-methyl-phenyl ester (3.93 g, 9 mmol, from above) was dissolved in a mixture of tetrahydrofuran (25 mL), methanol (50 mL) and aqueous 1N sodium hydroxide (9 mL, 9 mmol). The mixture was stirred at room temperature for 18 hours. The mixture was then concentrated under reduced pressure to remove most of the organic solvent. The resulting suspension was then diluted with water (45 mL) and saturated aqueous sodium bicarbonate solution (5 mL). After standing for 30 minutes, precipitate was collected, washed with water and dried to give crude 3-chloro-4-fluoro-N-(3-hydroxy-4-methyl-phenyl)-benzamide as a white powder. (Yield 2.59 g).
Workup
- concentrationThe mixture was then concentrated under reduced pressure
- customto remove most of the organic solvent
- additionThe resulting suspension was then diluted with water (45 mL) and saturated aqueous sodium bicarbonate solution (5 mL)
- waitAfter standing for 30 minutes
- customprecipitate was collected
- washwashed with water
- customdried
Sources & evidence
- ORD record
- ord-e3c521eba04b4ac6be478531a802dcaf
- Source dataset
- uspto-grants-2011_06
- Patent number
- US07968554B2
Reaction notes
Loading…