Methanol → methyl 4-methylnicotinate

HRID 2204510Notes

Reaction equation

HRID 2204510 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-5ce128ea16e5461498440d64b3cdd4bf
Source dataset
uspto-grants-2016_06
Patent number
US09365579B2

Reaction notes

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