ChemicalBook CAS DataBase List Methyl 6-chloronicotinate

Methyl 6-chloronicotinate synthesis

13synthesis methods

Product Name:Methyl 6-chloronicotinate
CAS Number:73781-91-6
Molecular formula:C7H6ClNO2
Molecular Weight:171.58

67-56-1 Synthesis

67-56-1
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$7.29/5ml-f

5326-23-8 Synthesis

5326-23-8
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$5.00/1g

73781-91-6
278 suppliers
$5.00/1g

Yield:73781-91-6 91%

Reaction Conditions:

Stage #1:6-Chloro-3-pyridinecarboxylic acid with oxalyl dichloride;N,N-dimethyl-formamide at 20; for 16 h;
Stage #2:methanol in dichloromethane at 40; for 0.25 h;

Steps:

1 Methyl 6-chloronicotinate (7)
To a cooled (0 ° C.) solution of 7 6-chloronicotinic acid 6 (200 mg, 1.29 mmol) in 8 CH₂Cl₂(5 mL), 2 drops of 9 DMF and 10 oxalyl Chloride (0.13 mL, 1.52 mmol) was added drop wise. The reaction mixture was stirred at room temperature for 16 h and the volatiles were removed under reduced pressure. The residue was cooled to 0° C. and dissolved in CH₂Cl₂(5 mL), 11 methanol (1 mL) and heated to 40° C. (monitored by TLC). After 15 min, the solvents were removed under vacuo, diluted with ether. The organic layer was washed with water and brine solution. The organic extracts were dried over anhydrous Na₂SO₄and concentrated under reduced pressure, to afford 12 methyl 6-chloronicotinate 7 (200 mg, 91%) as off-white solid. ¹H NMR (400 MHz, CDCl₃): δ 9.00 (s, 1H), 8.26 (d, J=8.4 Hz, 1H), 7.43 (d, J=8.4 Hz, 1H), 3.96 (s, 3H).

References:

Sham, Yuk Yin;Muthyala, Ramaiah;Shin, Woo-Shik US2018/369217, 2018, A1 Location in patent:Paragraph 0066

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