Water → Ethyl 2-(1,2-dihydro-2-oxopyridine-1-ylmethyl)-6,7-dimethoxy-4-(3,4-dimethoxyphenyl)quinoline-3-carboxylate

HRID 862647Notes

Reaction equation

HRID 862647 reaction equation
[H-].[Na+].[OH:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][N:5]=1.[CH3:10][O:11][C:12]1[CH:13]=[C:14]2[C:19](=[CH:20][C:21]=1[O:22][CH3:23])[N:18]=[C:17]([CH2:24]I)[C:16]([C:26]([O:28][CH2:29][CH3:30])=[O:27])=[C:15]2[C:31]1[CH:36]=[CH:35][C:34]([O:37][CH3:38])=[C:33]([O:39][CH3:40])[CH:32]=1.O>CN(C)C=O>[O:3]=[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][N:5]1[CH2:24][C:17]1[C:16]([C:26]([O:28][CH2:29][CH3:30])=[O:27])=[C:15]([C:31]2[CH:36]=[CH:35][C:34]([O:37][CH3:38])=[C:33]([O:39][CH3:40])[CH:32]=2)[C:14]2[C:19](=[CH:20][C:21]([O:22][CH3:23])=[C:12]([O:11][CH3:10])[CH:13]=2)[N:18]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 21851133Ethyl 2-iodomethyl-6,7-dimethoxy-4-(3,4-dimethoxyphenyl)quinoline-3-carboxylateHCID 178516071HCID 178516071, compound

Product 1

HCID 22097577Ethyl 2-(1,2-dihydro-2-oxopyridine-1-ylmethyl)-6,7-dimethoxy-4-(3,4-dimethoxyphenyl)quinoline-3-carboxylateYield 57%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Oily sodium hydride (60%, 0.117 g) was added to a solution of 2-hydroxypyridine (0.277 g) in N,N-dimethylformamide (DMF)(10 ml), and the mixture was stirred at room temperature for 15 minutes. To this solution was added ethyl 6,7-dimethoxy-4-(3,4-dimethoxyphenyl)-2-iodomethylquinoline-3-carboxylate(1.2 g) . The mixture was stirred at room temperature for 8 hours, 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 residual oil was subjected to column chromatography on silica gel. The fractions eluted with chloroform/ethyl acetate (10/1, v/v) gave ethyl 2-(1,2-dihydro-2-oxopyridine-1-ylmethyl)-6,7-dimethoxy-4-(3,4-dimethoxyphenyl)quinoline-3-carboxylate (0.64 g, 57%) which was then recrystallized from ethanol. Colorless prisms. mp. 154°-156° C.

Workup

  1. stirringThe mixture was stirred at room temperature for 8 hours
  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 (10/1

Sources & evidence

ORD record
ord-f072b7ae4e7d4264911722a62d5defa3
Source dataset
uspto-grants-1998_02
Patent number
US05719157

Reaction notes

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