Thionyl Chloride → 3-(Pyridin-3-yl)benzoyl chloride

HRID 415296노트

반응식

HRID 415296 반응식
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[CH:8]=[C:9]([CH:13]=[CH:14][CH:15]=2)[C:10](O)=[O:11])[CH:2]=1.S(Cl)([Cl:18])=O>>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[CH:8]=[C:9]([CH:13]=[CH:14][CH:15]=2)[C:10]([Cl:18])=[O:11])[CH:2]=1

참가 물질

3

반응물 2

HCID 24386Thionyl ChlorideHCID 27955753-(Pyridin-3-yl)benzoic acid

생성물 1

HCID 866330953-(Pyridin-3-yl)benzoyl chloride

실험 절차

Thionyl chloride (10 mL) was added to 3-(pyridin-3-yl)benzoic acid (1.5 g, 7.5 mmol) and the mixture was stirred under reflux overnight. The solvent was evaporated under reduced pressure and the residue was dried in vacuum giving 1.5 g crude 3-(pyridin-3-yl)benzoyl chloride. To a solution of methyl 3-amino-2-hydroxybenzoate (950 mg, 5.8 mmol) and pyridine (480 mg, 6 mmol) in toluene (50 mL) was added 3-(pyridin-3-yl)benzoyl chloride (1.5 g, 7 mmol) portion-wise at 0° C. and then stirred at 70° C. for 4 h. The resulting mixture was extracted with ethyl acetate (100 mL×4), the organic phase was washed with water and saturated sodium bicarbonate, dried with anhydrous sodium sulfate and evaporated under reduced pressure to obtain methyl 2-hydroxy-3-(3-(pyridin-3-yl)benzamido)benzoate as a yellow solid (1.8 g, yield 85%). LC-MS (ESI) m/z: 349 (M+1)+.

후처리

  1. temperatureunder reflux overnight
  2. customThe solvent was evaporated under reduced pressure
  3. customthe residue was dried in vacuum

출처 및 근거

ORD 기록
ord-6181ec2237c94cf6913032f821cdabe7
출처 데이터셋
uspto-grants-2012_01
특허 번호
US08088760B2

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