Methyl 6-chloronicotinate synthesis
- Product Name:Methyl 6-chloronicotinate
- CAS Number:73781-91-6
- Molecular formula:C7H6ClNO2
- Molecular Weight:171.58
67-56-1
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$7.29/5ml-f
5326-23-8
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$5.00/1g
73781-91-6
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$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 Na2SO4 and 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
17874-79-2
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73781-91-6
291 suppliers
$5.00/1g
5326-23-8
573 suppliers
$5.00/1g
73781-91-6
291 suppliers
$5.00/1g
5326-23-8
573 suppliers
$5.00/1g
18107-18-1
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$33.00/5g
73781-91-6
291 suppliers
$5.00/1g