Glycerol → Methyl 6-quinolineacetate

Temperature

140 °C

Sulphuric acid (67.5 ml) was added to 4-Aminophenylacetic acid (45 g, 297 mmol), glycerol (61.7 g, 67 mmol), and iodine (1.14 g, 4 mmol) drop-wise at rt. The mixture was heated to 140° C. for 24 h. After that reaction mixture cooled to rt and pH adjusted to 5 using 10% sodium hydroxide solution. To this methanol (350 ml) and sulphuric acid (3 ml) was added and heated to 100° C. for 24 h. Reaction mixture filtered through celite and filtrate was evaporated on rotavapour to obtain the residue. pH of the residue was adjusted to 5 using 4% NaOH solution and extracted with EtOAc. EtOAc layer was dried on anhydrous Na2SO4 and EtOAc removed on rotavapour to obtain the crude. Crude was purified by column using EtOAc and Petether as eluent to obtain methyl-2-(quinolin-6-yl)acetate (11.2 g). Methyl-2-(quinolin-6-yl)acetate (11.2 g) was dissolved in Methanol (8 ml) and water (8 ml) and added sodium hydroxide (3.3 g, 82 mmol). This mixture stirred for 30 mins and methanol removed on rotavapour to obtain the residue. Residue was acidified to pH 5 using 0.8 N HCl to obtain the solid. Solid was filtered and dried to obtain the title compound (8.2 g).

1. temperatureAfter that reaction mixture cooled to rt
2. temperatureheated to 100° C. for 24 h
3. customReaction mixture
4. filtrationfiltered through celite and filtrate
5. customwas evaporated on rotavapour
6. customto obtain the residue
7. extractionextracted with EtOAc
8. dry with materialEtOAc layer was dried on anhydrous Na2SO4 and EtOAc
9. customremoved on rotavapour
10. customto obtain the crude
11. customCrude was purified by column

ORD record

ord-5c3777c02e66404595ddc32402756255

Source dataset

uspto-grants-2015_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08993612B2