ChemicalBook CAS DataBase List Methyl 6-methylnicotinate

Methyl 6-methylnicotinate synthesis

9synthesis methods

Product Name:Methyl 6-methylnicotinate
CAS Number:5470-70-2
Molecular formula:C8H9NO2
Molecular Weight:151.16

67-56-1 Synthesis

67-56-1
745 suppliers
$9.00/25ml

3222-47-7 Synthesis

3222-47-7
345 suppliers
$6.00/1g

5470-70-2
523 suppliers
$5.00/5g

Yield:5470-70-2 75%

Reaction Conditions:

with sulfuric acid for 17 h;Reflux;

Steps:

3.1 [0153] Step 1: 6-Methyl-nicotinic acid methyl ester

[0154] To a stirred solution of compound I (40 g; 290 mmol; 1 eq) in methanol (0.75 L) was added sulfuric acid (40 mL) and the resulting mixture was heated at reflux for 17 h. The mixture was then evaporated to dryness and the pH was adjusted to 7 using saturated ice-cold aqueous NaHCO3 solution and solid NaHCO3. The organic components were extracted from the aqueous layer with ethyl acetate (3 x 500 mL) and the combined organic layers were washed with brine, dried over anhydrous sodium sulfate, filtered and the solvent was removed in vacuo to afford the title compound (33 g, 75%) as an off-white solid. 1H NMR (CDC13) ? 9.06 (s, 1H), 8.13 (dd, 1H, J = 2, 8 Hz), 7.20 (d, 1H, J = 8 Hz), 3.89 (s, 3H), 2.58 (s, 3H). LCMS: m/z = 152.4 [M+Hj , RT = 2.36 minutes, (Program P1, Column W).

References:

WO2015/95128,2015,A1 Location in patent:Paragraph 0152; 0153; 0154