Thionyl Chloride → 3-(Pyridin-2-yl)benzoyl chloride

HRID 415290노트

반응식

HRID 415290 반응식
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[CH:8]=[C:9]([CH:13]=[CH:14][CH:15]=1)[C:10](O)=[O:11].S(Cl)([Cl:18])=O>>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[CH:8]=[C:9]([CH:13]=[CH:14][CH:15]=1)[C:10]([Cl:18])=[O:11]

참가 물질

3

반응물 2

HCID 24386Thionyl ChlorideHCID 51525923-(Pyridin-2-yl)benzoic acid

생성물 1

HCID 177955953-(Pyridin-2-yl)benzoyl chloride

실험 절차

Thionyl chloride (10 mL) was added to 3-(pyridin-2-yl)benzoic acid (1.69 g, 8.5 mmol) and the mixture was stirred under reflux overnight. The solvent was evaporated under reduced pressure and the residue was dried in vacuum to give 3-(pyridin-2-yl)benzoyl chloride. 1.66 g of crude product was obtained. To a solution of methyl 3-amino-2-hydroxybenzoate (0.84 g, 5 mmol) and pyridine (790 mg, 10 mmol) in toluene (50 mL) were added crude 3-(pyridin-2-yl)benzoyl chloride (1.6 g, 7.37 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 yellow solid of methyl 2-hydroxy-3-(3-(pyridin-2-yl)benzamido)benzoate (1.48 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-68b13b4be3f84180b274b4a4d1516b40
출처 데이터셋
uspto-grants-2012_01
특허 번호
US08088760B2

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