4-Hydroxy-N-methylcarbostyril → 1-methyl-4-butoxyquinolin-2(1H)-one

To a solution of 10.0 g. of 1-methyl-4-hydroxyquinolin-2(1H)-one in 150 ml. of dimethylformamide is added 2.4 g. of pentane washed with sodium hydride and the resulting mixture stirred for 2 hours at room temperature. There is then added 10.6 g. of n-butyl iodide and the resulting mixture is stirred for 24 hours at room temperature. The reaction mixture is then poured onto 1.3 liters of cold water, extracted with ethyl acetate, washed 3 times with water, dried, charcoaled, filtered and evaporated in vacuo. The resulting oil is dissolved in 120 ml. of ether and cooled in an acetone/dry ice bath to crystallize solids which are filtered off and washed with cold ether to obtain 1-methyl-4-butoxyquinolin-2(1H)-one, m.p. 77°-80° C.

1. washof pentane washed with sodium hydride
2. additionThere is then added 10.6 g
3. stirringof n-butyl iodide and the resulting mixture is stirred for 24 hours at room temperature
4. additionThe reaction mixture is then poured onto 1.3 liters of cold water
5. extractionextracted with ethyl acetate
6. washwashed 3 times with water
7. customdried
8. filtrationfiltered
9. customevaporated in vacuo
10. dissolutionThe resulting oil is dissolved in 120 ml
11. temperatureof ether and cooled in an acetone/dry ice bath
12. customto crystallize solids which
13. filtrationare filtered off
14. washwashed with cold ether

ORD record

ord-75d29954081e41ebb90f702facca026f

Source dataset

uspto-grants-1980_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04190659