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

HRID 1788331Notes

Reaction equation

HRID 1788331 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 CH2Cl2 (200 mL) cooled to 0° C. is added MeOH (10 mL), 4-dimethylaminopyridine (11.6 g, 94.8 mmol), and EDC (18.2 g, 94.8 mmol). The mixture is stirred at RT for 6 h, washed with water and brine, and dried over Na2SO4. The mixture is filtered and concentrated in vacuo and the residue is chromatographed on silica gel (50% EtOAc/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 Na2SO4
  3. filtrationThe mixture is filtered
  4. concentrationconcentrated in vacuo
  5. customthe residue is chromatographed on silica gel (50% EtOAc/Hexanes)

Sources & evidence

ORD record
ord-cf9535f6b3cf4b6b98d9b139abe041d0
Source dataset
uspto-grants-2009_03
Patent number
US07511065B2

Reaction notes

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