Cesium carbonate → Methyl 5-methoxypyridine-3-carboxylate

HRID 2264156Notes

Reaction equation

HRID 2264156 reaction equation
[OH:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8].[C:12](=O)([O-])[O-].[Cs+].[Cs+]>[Cl-].C1([N+](C)(C)C)C=CC=CC=1.C(#N)C>[CH3:12][O:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8]

Participants

5

Reactant 2

HCID 10796Cesium carbonateHCID 354317Methyl 5-hydroxypyridine-3-carboxylate

Product 1

HCID 16218325Methyl 5-methoxypyridine-3-carboxylate

Reagents, catalysts & solvents 2

HCID 67309Phenyltrimethylammonium chlorideCatalystHCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 0.5 g of methyl 5-hydroxynicotinate, 1.2 g (2 equiv) of phenyltrimethylammonium chloride, 4.8 g (3 equiv) of cesium carbonate, and 5 mL of anhydrous acetonitrile was heated to 80° C. for 6 h, cooled, filtered and concentrated under reduced pressure. The residue was taken up in 25 mL of ethyl acetate, filtered and concentrated. Purification by flash chromatography (0-50% ethyl acetate in hexane) gave the product as white crystalline solid: MS (m+1)=168.1; 1H NMR (400 MHz, CDCl3) 8.72 (s, 1H), 8.4 (s, 1H), 7.67 (s, 1H), 3.83 (s, 3H), 3.82 (s, 3H).

Workup

  1. temperaturecooled
  2. filtrationfiltered
  3. concentrationconcentrated under reduced pressure
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customPurification by flash chromatography (0-50% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-15cb9dd0846b45f9a55572fac05a226f
Source dataset
uspto-grants-2010_12
Patent number
US07855201B2

Reaction notes

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