Water → Methyl 2-[(2-methyl-4-quinolyl)thio]acetate

2-methylquinoline-4-thiol 5a (1.00 g, 5.71 mmol, 1.00 eq.) was dissolved in dimethylformamide (10 mL) at room temperature. Potassium carbonate (0.87 g, 6.28 mmol, 1.10 eq.) was added and the mixture was stirred for 15 minutes. Methyl bromoacetate (921 mg, 6.02 mmol, 1.05 eq.) was added dropwise to the solution, and the reaction was stirred at room temperature for 2.5 hours. Water (20 mL) was added to the reaction mixture, and the aqueous layer was extracted with ethyl acetate (30 mL). The aqueous layer was further extracted with ethyl acetate (3×50 mL), and the combined organic layers were dried over magnesium sulfate, filtered and concentrated in vacuo. The resulting residue was dried on high vacuum to yield 5b as a brown solid (1.25 g, 88%).

1. stirringthe reaction was stirred at room temperature for 2.5 hours
2. extractionthe aqueous layer was extracted with ethyl acetate (30 mL)
3. extractionThe aqueous layer was further extracted with ethyl acetate (3×50 mL)
4. dry with materialthe combined organic layers were dried over magnesium sulfate
5. filtrationfiltered
6. concentrationconcentrated in vacuo
7. customThe resulting residue was dried on high vacuum

ORD record

ord-25b9b7122d184010ab7bd0f797da9ee3

Source dataset

uspto-grants-2012_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08278327B2