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

HRID 437760Notes

Reaction equation

HRID 437760 reaction equation
[CH3:1][N:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([OH:12])=[CH:4][C:3]1=[O:13]>CN(C)C=O>[CH3:1][N:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([O:12][CH2:3][CH2:4][CH2:5][CH3:6])=[CH:4][C:3]1=[O:13]

Participants

3

Reactant 1

HCID 546864364-Hydroxy-N-methylcarbostyril

Product 1

HCID 129266601-methyl-4-butoxyquinolin-2(1H)-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-3c3012dda2fe4917830a061662a299b5
Source dataset
uspto-grants-1977_06
Patent number
US04032528

Reaction notes

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