Sodium hydride → HCID 19006256, compound

HRID 1743037Notes

Reaction equation

HRID 1743037 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([C:7]2[C:16]3[C:11](=[CH:12][C:13]([OH:19])=[C:14]([O:17][CH3:18])[CH:15]=3)[CH:10]=[C:9]([C:20]([O:22][CH3:23])=[O:21])[C:8]=2[C:24]([O:26][CH3:27])=[O:25])=[CH:3][CH:2]=1.[H-].[Na+].[CH3:30][O:31][CH2:32][CH2:33]I>CN(C)C=O>[N:1]1[CH:6]=[CH:5][C:4]([C:7]2[C:16]3[C:11](=[CH:12][C:13]([O:19][CH2:33][CH2:32][O:31][CH3:30])=[C:14]([O:17][CH3:18])[CH:15]=3)[CH:10]=[C:9]([C:20]([O:22][CH3:23])=[O:21])[C:8]=2[C:24]([O:26][CH3:27])=[O:25])=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 791361-Iodo-2-methoxyethaneHCID 22007379HCID 22007379, compound

Product 1

HCID 19006256HCID 19006256, compoundYield 43.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 1-(4-pyridyl)-2,3-bis(methoxycarbonyl)-6-hydroxy-7-methoxynaphthalene (17 g) in dimethylformamide (50 ml) is added gradually sodium hydride (60% dispersion-type) under ice-cooling, and the mixture is stirred at room temperature for 30 minutes. The mixture is cooled with ice, and thereto is added 2-methoxyethyl iodide (10.3 g). The mixture is stirred at room temperature for 2 hours, and heated to 80° C. One hour thereafter, the reaction solution is allowed to cool, and concentrated. The resulting residue is dissolved in ethyl acetate, washed with water, dried, and concentrated. The precipitated crystal is washed with diethyl ether to give 1-(4-pyridyl)-2,3-bis(methoxycarbonyl)-6-(2-methoxyethyloxy)-7-methoxynaphthalene (8.5 g).

Workup

  1. temperaturecooling
  2. temperatureThe mixture is cooled with ice
  3. stirringThe mixture is stirred at room temperature for 2 hours
  4. temperatureheated to 80° C
  5. customOne hour
  6. temperatureto cool
  7. concentrationconcentrated
  8. dissolutionThe resulting residue is dissolved in ethyl acetate
  9. washwashed with water
  10. customdried
  11. concentrationconcentrated
  12. washThe precipitated crystal is washed with diethyl ether

Sources & evidence

ORD record
ord-050fe9ad7d474af390e8113320732611
Source dataset
uspto-grants-1994_08
Patent number
US05342941

Reaction notes

Loading…