Pyridine → methyl 2-fluoro-3-(N-methylbenzamido)benzoate

HRID 534669ノート

反応式

HRID 534669 の反応式
[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]

参加物

6

反応物 4

HCID 1049PyridineHCID 7412Benzoyl chlorideHCID 8857Ethyl AcetateHCID 200866302-Fluoro3-(methylamino)benzoic acid

生成物 1

HCID 58298654methyl 2-fluoro-3-(N-methylbenzamido)benzoate収率 64%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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.

後処理

  1. customto react for 12 hours at room temperature
  2. washthe mixture was washed sequentially with water
  3. dry with materiala 1N hydrochloric acid, a saturated aqueous solution of sodium bicarbonate, and saturated saline, and then dried over anhydrous sodium sulfate
  4. filtrationThe sodium sulfate was filtered away
  5. customthe concentration residue was purified by silica gel column chromatography (developer solvent: ethyl acetate/n-hexane=1/8)

出典と根拠

ORDレコード
ord-414311e9b3904f858acb14c0f12fb19a
出典データセット
uspto-grants-2014_10
特許番号
US08853440B2

反応ノート

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