Isopropyl iodide → HCID 13885754, compound

HRID 580009Notes

Reaction equation

HRID 580009 reaction equation
[H-].[Na+].[CH3:3][C:4]1[NH:5][C:6]2[CH:7]=[CH:8][NH:9][C:10](=[O:24])[C:11]=2[CH:12]([C:19]2[S:20][CH:21]=[CH:22][CH:23]=2)[C:13]=1[C:14]([O:16][CH2:17][CH3:18])=[O:15].[CH:25](I)([CH3:27])[CH3:26]>CN(C)C=O>[CH:25]([O:24][C:10]1[N:9]=[CH:8][CH:7]=[C:6]2[C:11]=1[CH:12]([C:19]1[S:20][CH:21]=[CH:22][CH:23]=1)[C:13]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[C:4]([CH3:3])[NH:5]2)([CH3:27])[CH3:26]

Participants

5

Reactant 3

HCID 6362Isopropyl iodideHCID 24758Sodium hydrideHCID 13389016HCID 13389016, compound

Product 1

HCID 13885754HCID 13885754, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2.1 g (70 mMole) sodium hydride (80% in oil) are suspended in 100 ml dry dimethylformamide and, while stirring at ambient temperature, 20 g (63 mMole) ethy (±)-1,4,5,6-tetrahydro-2-methyl-5-oxo-4-(2-thienyl)-1,6-naphthyridine-3-carboxylate are added thereto portionwise. After cessation of the gas evolution, the reaction mixture is further stirred for 30 minutes at ambient temperature. 16 g (94 mMole) isopropyl iodide in 30 ml diemthylformamide are then added thereto. The reaction mixture is stirred for two days at ambient temperature, the solvent is removed in a vacuum and the residue is taken up with water and ethyl acetate. After shaking up, the ethyl acetate phase is separated off and dried over anhydrous magnesium sulphate. After distilling off the solvent, the residue obtained is separated chromatographically on silica gel with toluene/ethyl acetate (3:1 v/v). The fraction with the Rf of 0.3 is isolated and recrystallized from n-hexane. There is obtained ethyl (±)-1,4-dihydro-5-isopropoxy-2-methyl-4-(2-thienyl)-1,6-naphthyridine-3 -carboxylate in the form of colorless crystals; mp 110°-111° C.

Workup

  1. stirringAfter cessation of the gas evolution, the reaction mixture is further stirred for 30 minutes at ambient temperature
  2. stirringThe reaction mixture is stirred for two days at ambient temperature
  3. customthe solvent is removed in a vacuum
  4. stirringAfter shaking up
  5. customthe ethyl acetate phase is separated off
  6. dry with materialdried over anhydrous magnesium sulphate
  7. distillationAfter distilling off the solvent
  8. customthe residue obtained
  9. customis separated chromatographically on silica gel with toluene/ethyl acetate (3:1 v/v)
  10. customThe fraction with the Rf of 0.3 is isolated
  11. customrecrystallized from n-hexane

Sources & evidence

ORD record
ord-0c2d71ebcde4416f8989878c3fde8c93
Source dataset
uspto-grants-1988_06
Patent number
US04751228

Reaction notes

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