Methanol → methyl 4-methylnicotinate

HRID 1854359Notes

Reaction equation

HRID 1854359 reaction equation
[CH3:1][C:2]1[C:7]([C:8]([OH:10])=[O:9])=[CH:6][N:5]=[CH:4][CH:3]=1.OS(O)(=O)=O.[CH3:16]O>>[CH3:1][C:2]1[C:7]([C:8]([O:10][CH3:16])=[O:9])=[CH:6][N:5]=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 2291634-Methylnicotinic acid

Product 1

HCID 10877301methyl 4-methylnicotinateYield 94%

Procedure

A solution of 4-methylnicotinic acid (2.00 g, 14.6 mmol) and concentrated H2SO4 (4.66 mL, 87.6 mmol) in MeOH (50 mL) was heated at about 60° C. for about 16 h. The reaction was concentrated under reduced pressure then partitioned with EtOAc (150 mL) and saturated aqueous NaHCO3 (200 mL). The organic layer was dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure to a constant weight to afford methyl 4-methylnicotinate as a clear liquid (2.30 g, 94%): LC/MS (Table 2, Method a) Rt=1.67 min; MS m/z: 152 (M+H)+.

Workup

  1. concentrationThe reaction was concentrated under reduced pressure
  2. customthen partitioned with EtOAc (150 mL) and saturated aqueous NaHCO3 (200 mL)
  3. dry with materialThe organic layer was dried over anhydrous Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure to a constant weight

Sources & evidence

ORD record
ord-286200668d944bc286c2bb62d44d5be1
Source dataset
uspto-grants-2015_02
Patent number
US08962629B2

Reaction notes

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