Oxalyl chloride → Methyl 3-(3-pyridinyl)benzoate

HRID 906824Notes

Reaction equation

HRID 906824 reaction equation
[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]([OH:12])=[O:11])[CH:2]=1.[C:16](Cl)(=O)C(Cl)=O>C(Cl)Cl.CO>[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:12][CH3:16])=[O:11])[CH:2]=1

Participants

5

Reactant 2

HCID 65578Oxalyl chlorideHCID 27955753-(Pyridin-3-yl)benzoic acid

Product 1

HCID 4133188Methyl 3-(3-pyridinyl)benzoateYield 99%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a suspension of 3-(pyridin-3-yl)benzoic acid (0.8 g, 4 mmol) and N,N-dimethylformide (2 drops) in anhydrous methylene chloride (30 mL) was added oxalyl chloride (0.42 mL, 4.8 mmol) dropwise at 0° C. under argon. The mixture was stirred at RT for 3.5 hr and then concentrated. The yellow solid obtained was dissolved in anhydrous methanol (20 mL) at 0° C. After stirring at RT for 30 min, the mixture was concentrated. The residue was dissolved in ethyl acetate, washed with saturated aqueous sodium bicarbonate solution, brine, and dried over anhydrous sodium sulfate. Concentration gave 0.84 g (99% yield) of methyl 3-(pyridin-3-yl)benzoate as a yellow solid. (M+H)+=214.16.

Workup

  1. concentrationconcentrated
  2. customThe yellow solid obtained
  3. stirringAfter stirring at RT for 30 min
  4. concentrationthe mixture was concentrated
  5. dissolutionThe residue was dissolved in ethyl acetate
  6. washwashed with saturated aqueous sodium bicarbonate solution, brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. concentrationConcentration

Sources & evidence

ORD record
ord-5ecc281ef2474d3b9a31637ec5e7f10d
Source dataset
uspto-grants-2011_09
Patent number
US08013004B2

Reaction notes

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