Water → Ethyl 4-(3,4-dimethoxyphenyl)-6,7-dimethoxy-2-thiomorpholinomethylquinoline-3-carboxylate

HRID 1458941Notes

Reaction equation

HRID 1458941 reaction equation
[H-].[Na+].[NH:3]1[CH2:8][CH2:7][S:6][CH2:5][CH2:4]1.Cl[CH2:10][C:11]1[C:20]([C:21]([O:23][CH2:24][CH3:25])=[O:22])=[C:19]([C:26]2[CH:31]=[CH:30][C:29]([O:32][CH3:33])=[C:28]([O:34][CH3:35])[CH:27]=2)[C:18]2[C:13](=[CH:14][C:15]([O:38][CH3:39])=[C:16]([O:36][CH3:37])[CH:17]=2)[N:12]=1.O>CN(C)C=O>[CH3:35][O:34][C:28]1[CH:27]=[C:26]([C:19]2[C:18]3[C:13](=[CH:14][C:15]([O:38][CH3:39])=[C:16]([O:36][CH3:37])[CH:17]=3)[N:12]=[C:11]([CH2:10][N:3]3[CH2:8][CH2:7][S:6][CH2:5][CH2:4]3)[C:20]=2[C:21]([O:23][CH2:24][CH3:25])=[O:22])[CH:31]=[CH:30][C:29]=1[O:32][CH3:33]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 67164ThiomorpholineHCID 10813243Ethyl 2-chloromethyl-4-(3,4-dimethoxyphenyl)-6,7-dimethoxyquinoline-3-carboxylate

Product 1

HCID 22097633Ethyl 4-(3,4-dimethoxyphenyl)-6,7-dimethoxy-2-thiomorpholinomethylquinoline-3-carboxylateYield 42%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Oily sodium hydride (60%, 0.753 g) was added to a solution of thiomorpholine (1.8 g) in N,N-dimethylformamide (50 ml), and the mixture was stirred at room temperature for 15 minutes. Then ethyl 2-chloromethyl-4-(3,4-dimethoxyphenyl)-6,7-dimethoxyquinoline-3-carboxylate(6.0 g) was added. The resulting mixture was stirred at room temperature overnight, poured into water and extracted with ethyl acetate. The ethyl acetate layer was washed with water and dried over magnesium sulfate, and the solvent was evaporated. The residue was subjected to column chromatography on silica gel. The fractions eluted with chloroform/ethyl acetate (7/3, v/v) gave ethyl 4-(3,4-dimethoxyphenyl)-6,7-dimethoxy-2-thiomorpholinomethyl-quinoline-3-carboxylate (1.4 g, 42%) which was then recrystallized from ethanol. Colorless prisms. mp. 148°-149° C.

Workup

  1. stirringThe resulting mixture was stirred at room temperature overnight
  2. extractionextracted with ethyl acetate
  3. washThe ethyl acetate layer was washed with water
  4. dry with materialdried over magnesium sulfate
  5. customthe solvent was evaporated
  6. washThe fractions eluted with chloroform/ethyl acetate (7/3

Sources & evidence

ORD record
ord-ab3e6b76cd4f46c9ab57dcc60331bf22
Source dataset
uspto-grants-1998_12
Patent number
US05852039

Reaction notes

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