ChemicalBook CAS DataBase List 7-chloroquinoline-4-carboxylic acid

7-chloroquinoline-4-carboxylic acid synthesis

8synthesis methods

Product Name:7-chloroquinoline-4-carboxylic acid
CAS Number:13337-66-1
Molecular formula:C10H6ClNO2
Molecular Weight:207.61

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Yield: 60%

Reaction Conditions:

with sodium hydroxide in methanol at 68;Inert atmosphere;

Steps:

103.3; 104.3 [426] Step 3. 7-chloroquinoline-4-carboxylic acid
[427] Into a 100-mL round-bottom flask, was placed 7-chloroquinoline-4-carbonitrile (250 mg, 1.33 mmol, 1.00 equiv), sodium hydroxide(4N) (2 mL), methanol (10 mL). The resulting solution was stirred overnight at 68 °C. The reaction mixture was cooled to 10 °C. The resulting mixture was concentrated under vacuum. The resulting solution was diluted with H2O (50 mL). The resulting solution was extracted with ethyl acetate (50 mL x 3) and the aqueous layers combined. The pH value of the solution was adjusted to 6 with hydrochloric acid (3 mol/L). The solids were collected by filtration. This resulted in 165 mg (60%) of 7-chloroquinoline-4-carboxylic acid as a gray solid. MS (ES, m/z) [M+H]+: 208.

References:

THE ROCKEFELLER UNIVERSITY;PONDA, Manish, P.;BRESLOW, Jan, L.;SELNICK, Harold;EGBERTSON, Melissa WO2017/205296, 2017, A1 Location in patent:Paragraph 427