Thionyl Chloride → 3-(Pyridin-4-yl)benzoyl chloride

HRID 415301Notes

Reaction equation

HRID 415301 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([C:7]2[CH:8]=[C:9]([CH:13]=[CH:14][CH:15]=2)[C:10](O)=[O:11])=[CH:3][CH:2]=1.S(Cl)([Cl:18])=O>>[N:1]1[CH:6]=[CH:5][C:4]([C:7]2[CH:8]=[C:9]([CH:13]=[CH:14][CH:15]=2)[C:10]([Cl:18])=[O:11])=[CH:3][CH:2]=1

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 27955623-(Pyridin-4-yl)benzoic acid

Product 1

HCID 866330963-(Pyridin-4-yl)benzoyl chloride

Procedure

Thionyl chloride (10 mL) was added to 3-(pyridin-4-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 of crude 3-(pyridin-4-yl)benzoyl chloride. To a solution of methyl 3-amino-2-hydroxybenzoate (950 g, 5.8 mmol) and pyridine (480 mg, 6 mmol) in toluene (50 mL) was added crude 3-(pyridin-4-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-4-yl)benzamido)benzoate as a yellow solid (1.8 g, yield 85%). LC-MS (ESI) m/z: 349 (M+1)+.

Workup

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

Sources & evidence

ORD record
ord-213a886c14394d0e97c598303c4914e8
Source dataset
uspto-grants-2012_01
Patent number
US08088760B2

Reaction notes

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