Methyl 2-chloroquinoline-7-carboxylate synthesis
- Product Name:Methyl 2-chloroquinoline-7-carboxylate
- CAS Number:1416801-65-4
- Molecular formula:C11H8ClNO2
- Molecular Weight:221.64
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Yield:1416801-65-4 36 %
Reaction Conditions:
with oxalyl dichloride in dichloromethane at 0 - 50;
Steps:
1.333 Methyl 2-chloroquinoline-7-carboxylate (X-1865A3).
To a stirred solution of 7- (methoxycarbonyl)quinoline 1-oxide (X-1865A2) (4.50 g, 22.16 mmol) in a mixture of DMF- DCM (1:1; 90 mL) was added oxalyl chloride (8.44 g, 66.48 mmol) at 0 °C drop-wise and the reaction mixture was heated at 50 °C for 2h. Reaction mixture was quenched with an aqueous solution of saturated NaHCO3 (100 mL) and was extracted with dichloromethane (200 mL x 3). Combined organic extracts were dried over anhydrous Na2SO4 and concentrated under reduce pressure to afford crude mass which was purified by silica gel column chromatography, using ethyl acetate-hexane = 0:1 -> 1:9 as eluent, to afford methyl 2-chloroquinoline-7-carboxylate (X- 1865 A3) ( 1.8 g, 36%) as off-white solid. MS: [MH]+ 222.2.
References:
WO2022/204452,2022,A1 Location in patent:Paragraph 0001695; 0001698
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