Methanol → Methyl 6-cyanopyridine-3-carboxylate

HRID 76352Notes

Reaction equation

HRID 76352 reaction equation
[C:1]([C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=[O:8])=[CH:5][N:4]=1)#[N:2].O.[CH3:13]O>ClCCl.CN(C)C1C=CN=CC=1>[CH3:13][O:8][C:7](=[O:9])[C:6]1[CH:10]=[CH:11][C:3]([C:1]#[N:2])=[N:4][CH:5]=1

Participants

6

Reactant 3

HCID 887MethanolHCID 962WaterHCID 27611086-Cyanopyridine-3-carboxylic acid

Product 1

HCID 13144281Methyl 6-cyanopyridine-3-carboxylate

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

6-Cyanonicotinic acid (500 mg) was dissolved in dichloromethane (25 ml), water-soluble carbodiimide (776 mg), methanol (0.164 ml) and 4-dimethylaminopyridine (49 mg) were added thereto, and the mixture was stirred for 2 hr 10 min. The reaction mixture was washed successively with saturated aqueous sodium hydrogen carbonate and saturated brine and dried over anhydrous sodium sulfate. The solvent was evaporated, and the obtained residue was purified by column chromatography (Yamazen HI-FLASH™ COLUMN size 2 L, elution solvent: hexane/ethyl acetate) to give the title compound. The same reactions were repeated using 6-cyanonicotinic acid (547 mg) to give the title compound (total 951 mg).

Workup

  1. washThe reaction mixture was washed successively with saturated aqueous sodium hydrogen carbonate and saturated brine
  2. dry with materialdried over anhydrous sodium sulfate
  3. customThe solvent was evaporated
  4. customthe obtained residue was purified by column chromatography (Yamazen HI-FLASH™ COLUMN size 2 L, elution solvent: hexane/ethyl acetate)

Sources & evidence

ORD record
ord-ae72201310804c89ab9f15c7c33145e7
Source dataset
uspto-grants-2014_09
Patent number
US08835631B2

Reaction notes

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