Glycerol → 2-(Quinolin-6-yl)propanoic acid

The mixture of 2-(4-Amino-phenyl)-propionic acid (1.70 g), FeSO4 7H2O (0.30 g), glycerol (4.04 g) and sulfuric acid (2 mL) was refluxed with stirring for 5 h. After cooled to room temperature, the reaction mixture was concentrated under reduced vacuum. The aqueous solution was treated with 12N—NaOH solution. The precipitated solid was filtered and the filtrate was acidified with AcOH. The resulting mixture was extracted and the combined organic layer was dried over magnesium sulfate, filtered, concentrated in vacuo. The resulting residue was chromatographed on silica gel (CH2Cl2:MeOH=15:1 to 10:1) to afford the product as a brown solid. (0.83 g, 40.0%)

1. temperaturewas refluxed
2. concentrationthe reaction mixture was concentrated under reduced vacuum
3. additionThe aqueous solution was treated with 12N—NaOH solution
4. filtrationThe precipitated solid was filtered
5. extractionThe resulting mixture was extracted
6. dry with materialthe combined organic layer was dried over magnesium sulfate
7. filtrationfiltered
8. concentrationconcentrated in vacuo
9. customThe resulting residue was chromatographed on silica gel (CH2Cl2:MeOH=15:1 to 10:1)

ORD record

ord-dffa9e761764455ea7ee3b637a85aef5

Source dataset

uspto-grants-2011_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08084484B2