Pyridine → methyl 2-fluoro-3-(N-methylbenzamido)benzoate
Reaction equation
[F:1][C:2]1[C:10]([NH:11][CH3:12])=[CH:9][CH:8]=[CH:7]C=1C(O)=O.[C:13](Cl)(=[O:20])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.N1C=CC=CC=1.[C:28]([O:31][CH2:32]C)(=[O:30])[CH3:29]>O1CCCC1>[F:1][C:2]1[C:10]([N:11]([CH3:12])[C:13](=[O:20])[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:9][CH:8]=[CH:7][C:29]=1[C:28]([O:31][CH3:32])=[O:30]Participants
Procedure
2-Fluoro3-(methylamino)benzoic acid (1.42 g, 4.94 mmol) was dissolved in tetrahydrofuran (15 ml), and benzoyl chloride (0.83 g, 5.90 mmol) and pyridine (0.47 g, 5.94 mmol) were added thereto. The reaction mixture was allowed to react for 12 hours at room temperature. Ethyl acetate was added to the reaction solution, and the mixture was washed sequentially with water, a 1N hydrochloric acid, a saturated aqueous solution of sodium bicarbonate, and saturated saline, and then dried over anhydrous sodium sulfate. The sodium sulfate was filtered away, and the concentration residue was purified by silica gel column chromatography (developer solvent: ethyl acetate/n-hexane=1/8), as a result of which 1.42 g (yield: 64%) of the indicated compound was obtained.
Workup
- customto react for 12 hours at room temperature
- washthe mixture was washed sequentially with water
- dry with materiala 1N hydrochloric acid, a saturated aqueous solution of sodium bicarbonate, and saturated saline, and then dried over anhydrous sodium sulfate
- filtrationThe sodium sulfate was filtered away
- customthe concentration residue was purified by silica gel column chromatography (developer solvent: ethyl acetate/n-hexane=1/8)
Sources & evidence
- ORD record
- ord-414311e9b3904f858acb14c0f12fb19a
- Source dataset
- uspto-grants-2014_10
- Patent number
- US08853440B2
Reaction notes
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