Water → Ethyl 8-methoxycarbonyl-4-oxo-10-propyl-6(N-methyl-4-toluenesulphonamido)-4H-pyrano[3,2-g]quinoline-2-carboxylate

HRID 2417929Notes

Reaction equation

HRID 2417929 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:14]=[C:13]([NH:15][S:16]([C:19]2[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][CH:20]=2)(=[O:18])=[O:17])[C:12]2[C:7](=[C:8]([CH2:36][CH2:37][CH3:38])[C:9]3[O:29][C:28]([C:30]([O:32][CH2:33][CH3:34])=[O:31])=[CH:27][C:26](=[O:35])[C:10]=3[CH:11]=2)[N:6]=1)=[O:4].[C:39](=O)([O-])[O-].[K+].[K+].CI.O>CN1CCCC1=O>[CH3:1][O:2][C:3]([C:5]1[CH:14]=[C:13]([N:15]([CH3:39])[S:16]([C:19]2[CH:20]=[CH:21][C:22]([CH3:25])=[CH:23][CH:24]=2)(=[O:18])=[O:17])[C:12]2[C:7](=[C:8]([CH2:36][CH2:37][CH3:38])[C:9]3[O:29][C:28]([C:30]([O:32][CH2:33][CH3:34])=[O:31])=[CH:27][C:26](=[O:35])[C:10]=3[CH:11]=2)[N:6]=1)=[O:4]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 13352258HCID 13352258, compound

Product 1

HCID 20233205Ethyl 8-methoxycarbonyl-4-oxo-10-propyl-6(N-methyl-4-toluenesulphonamido)-4H-pyrano[3,2-g]quinoline-2-carboxylate

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

The product of step (a) (5.38 g, 0.01 mol) was suspended in N-methyl pyrrolidone (40 ml), and potassium carbonate (1.38 g, 0.01 mol) added, to give on stirring at room temperature for five minutes a deep red solution. Methyl iodide (2 ml) was then added, and the whole warmed to 40° C., and stirring continued for one hour. The solution was poured into water (150 ml), to give the sub-title compound on filtration, as a white powder, 5.44 g, (98.6%), m.p. 173°-174° C.

Workup

  1. customto give
  2. temperaturethe whole warmed to 40° C.
  3. stirringstirring
  4. waitcontinued for one hour

Sources & evidence

ORD record
ord-3fd575d1e3c745b5ad0e0ca56bd35cb4
Source dataset
uspto-grants-1984_09
Patent number
US04471119

Reaction notes

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