Methanol → HCID 59599757, compound

Temperature

100 °C

Quinolin-3-ol (500 mg, 3.44 mmol, 1.0 eq) is added at room temperature to a stirred solution of sodium hydroxide (1.6 g, 40.0 mmol, 11.6 eq) in chloroform (1 mL) and water (10 mL). After 2 hours stirring at 100° C., the reaction mixture is extracted with dichloromethane (3×20 mL) and water (20 mL) and the pH is adjusted to 4 by the addition of a 1N hydrochloric acid aqueous solution. The combined organic layers are dried over sodium sulfate, filtered and concentrated to give a residue that is purified by column chromatography (silica gel, eluent: dichloromethane:methanol, 200:1, v/v) to afford 3-hydroxy-quinoline-4-carbaldehyde as a yellow solid (60 mg, 10% yield).

1. extractionthe reaction mixture is extracted with dichloromethane (3×20 mL) and water (20 mL)
2. additionthe pH is adjusted to 4 by the addition of a 1N hydrochloric acid aqueous solution
3. dry with materialThe combined organic layers are dried over sodium sulfate
4. filtrationfiltered
5. concentrationconcentrated
6. customto give a residue that
7. customis purified by column chromatography (silica gel, eluent

ORD record

ord-afe79324206a48a2aa78ccbe3e519bee

Source dataset

uspto-grants-2015_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08927541B2