1,2-Dichloroethane → Methyl 6-methylpyridine-2-carboxylate

HRID 8209

Reaction equation

HRID 8209 reaction equation
[CH3:1][C:2]1[N:7]=[C:6]([C:8]([OH:10])=[O:9])[CH:5]=[CH:4][CH:3]=1.CO.[CH2:13](Cl)CCl>C(Cl)Cl.CN(C)C1C=CN=CC=1>[CH3:13][O:9][C:8]([C:6]1[CH:5]=[CH:4][CH:3]=[C:2]([CH3:1])[N:7]=1)=[O:10]

Participants

6

Reactant 3

HCID 111,2-DichloroethaneHCID 887MethanolHCID 702826-Methylpyridine-2-carboxylic acid

Product 1

HCID 73022Methyl 6-methylpyridine-2-carboxylate

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a suspension of 6-methyl-pyridine-2-carboxylic acid (10 g, 72.9 mmol) in methylene chloride (200 mL) cooled to 0° C. is added methanol (10 mL), 4-dimethylaminopyridine (11.6 g, 94.8 mmol), and EDC (18.2 g, 94.8 mmol). The mixture is stirred at room temperature for 6 h, washed with water and brine, and dried over sodium sulfate. The mixture is filtered and concentrated in vacuo. The residue is chromatographed on SiO2 (50% ethyl acetate/hexanes) to yield the title compound, 9.66 g (92%), as a colorless liquid.

Workup

  1. washwashed with water and brine
  2. dry with materialdried over sodium sulfate
  3. filtrationThe mixture is filtered
  4. concentrationconcentrated in vacuo
  5. customThe residue is chromatographed on SiO2 (50% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-6f91fd8aa044449a8fb53ad9db2adc17
Source dataset
uspto-grants-2006_08
Patent number
US07087626B2

Linked notes

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