Dimethylformamide → Methyl 3-methoxypyridine-2-carboxylate

HRID 884696Notes

Reaction equation

HRID 884696 reaction equation
[CH3:1][O:2][C:3]([C:5]1[C:10]([OH:11])=[CH:9][CH:8]=[CH:7][N:6]=1)=[O:4].[C:12]([O-])([O-])=O.[K+].[K+].CI.CN(C=O)C>CCOC(C)=O.O>[CH3:1][O:2][C:3]([C:5]1[C:10]([O:11][CH3:12])=[CH:9][CH:8]=[CH:7][N:6]=1)=[O:4]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 819341Methyl 3-Hydroxy-2-pyridinecarboxylate

Product 1

HCID 20474189Methyl 3-methoxypyridine-2-carboxylateYield 55.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

In a 50 mL round-bottom flask fitted with magnetic stirrer were placed 3-hydroxypyridine-2-carboxylic acid methyl ester (3.5 g, 22.80 mmol), K2CO3 (3.46 g, 25.0 mmol), MeI (4.87 g, 34.3 mmol) and DMF (20 mL). The reaction mixture was stirred for 18 h at rt under nitrogen. The reaction mixture was diluted with EtOAc (30 mL) and water (10 mL). The organic layer was separated and aqueous layer was extracted with EtOAc. The combined organic extracts were dried over Na2SO4 and concentrated to give the crude product. The crude product was purified by column chromatography using 30% EtOAc in hexane to give 2.1 g of 3-methoxypyridine-2-carboxylic acid methyl ester (54%).

Workup

  1. customIn a 50 mL round-bottom flask fitted with magnetic stirrer
  2. customThe organic layer was separated
  3. extractionaqueous layer was extracted with EtOAc
  4. dry with materialThe combined organic extracts were dried over Na2SO4
  5. concentrationconcentrated
  6. customto give the crude product
  7. customThe crude product was purified by column chromatography

Sources & evidence

ORD record
ord-e6df034704db4328b8887850f970a1fa
Source dataset
uspto-grants-2012_08
Patent number
US08242130B2

Reaction notes

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