Water → HCID 13544002, compound

HRID 904707Notes

Reaction equation

HRID 904707 reaction equation
[NH2:1][C:2]1[C:11]2[C:6](=[C:7]([CH2:22][CH2:23][CH3:24])[C:8]3[O:15][C:14]([C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:13][C:12](=[O:21])[C:9]=3[CH:10]=2)[N:5]=[C:4]([C:25]([O:27][CH2:28][CH3:29])=[O:26])[CH:3]=1.[H-].[Na+].I[CH3:33].O>CN(C)C=O>[CH3:33][NH:1][C:2]1[C:11]2[C:6](=[C:7]([CH2:22][CH2:23][CH3:24])[C:8]3[O:15][C:14]([C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:13][C:12](=[O:21])[C:9]=3[CH:10]=2)[N:5]=[C:4]([C:25]([O:27][CH2:28][CH3:29])=[O:26])[CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 14091432HCID 14091432, compound

Product 1

HCID 13544002HCID 13544002, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

Diethyl 6-amino-4-oxo-10-propyl-4H-pyrano[3,2-g]quinoline-2,8-dicarboxylate (0.4 g) was dissolved in dry dimethylformamide (15 ml), and added dropwise with stirring to a suspension of sodium hydride (50%, 0.053 g, washed with dry ether) in dry dimethylformamide (10 ml) under a dry nitrogen atomosphere. After about 30 minutes at ambient temperature a deep red colour had developed, and iodomethane (0.23 ml) was added dropwise and stirring continued at room temperature for a further five hours. The whole ws then poured into water and extracted with chloroform. The organic extracts were combined, dried over magnesium sulphate, evaporated in vacuo, and the resulting oil chromatographed on alumina to give the title compound (0.11 g), mp 235°-237° (from ethanol).

Workup

  1. additionadded dropwise
  2. waitcontinued at room temperature for a further five hours
  3. extractionextracted with chloroform
  4. dry with materialdried over magnesium sulphate
  5. customevaporated in vacuo
  6. customthe resulting oil chromatographed on alumina

Sources & evidence

ORD record
ord-7d73714e0dba4ad882a945706b60ffbe
Source dataset
uspto-grants-1983_12
Patent number
US04419352

Reaction notes

Loading…