Methanol → 8-methyl-6-[4-(N-n-propylcarbamoyloxy)phenyl]-2-(1H)-quinolone

HRID 568347Notes

Reaction equation

HRID 568347 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([C:13]2[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][CH:14]=2)[CH:5]=[C:6]2[C:11]=1[NH:10][C:9](=[O:12])[CH:8]=[CH:7]2.[CH2:20]([N:23]=[C:24]=[O:25])[CH2:21][CH3:22].CO>C1COCC1>[CH3:1][C:2]1[CH:3]=[C:4]([C:13]2[CH:18]=[CH:17][C:16]([O:19][C:24](=[O:25])[NH:23][CH2:20][CH2:21][CH3:22])=[CH:15][CH:14]=2)[CH:5]=[C:6]2[C:11]=1[NH:10][C:9](=[O:12])[CH:8]=[CH:7]2

Participants

5

Reactant 3

HCID 887MethanolHCID 61033Propyl isocyanateHCID 201504468-methyl-6-[4-hydroxylphenyl]-2-(1H)-quinolone

Product 1

HCID 201504508-methyl-6-[4-(N-n-propylcarbamoyloxy)phenyl]-2-(1H)-quinolone

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 8-methyl-6-[4-hydroxyphenyl]-2-(1H)-quinolone (0.30 g) and n-propylisocyanate (0.5 cm3) was heated under reflux in THF (10 cm3) under nitrogen for 50 hours. Methanol (10 cm3) was then added to dissolve solid material, followed by silica (Merck "MK 60.9385" [Trade Mark]) (10 g), and the volatile material was removed in vacuo. The residue was placed on top of a silica column (Merck "MK 60.9385") and eluted with chloroform:methanol, 19:1. Combination and evaporation of appropriate fractions in vacuo gave a solid which was recrystallised from propan-2-ol to afford the title compound, m.p. 224°-228°, (0.28 g).

Workup

  1. dissolutionto dissolve solid material
  2. customthe volatile material was removed in vacuo
  3. washeluted with chloroform
  4. customCombination and evaporation of appropriate fractions in vacuo
  5. customgave a solid which
  6. customwas recrystallised from propan-2-ol

Sources & evidence

ORD record
ord-08e752c9b4c842228435697a65fda5a8
Source dataset
uspto-grants-1988_03
Patent number
US04728654

Reaction notes

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