Dimethylformamide → Ethyl 6,7-dimethoxy-4-(3,4-dimethoxyphenyl)-2-[(2-methyl-6-pyridyl)oxymethyl]quinoline-3-carboxylate

HRID 617225Notes

Reaction equation

HRID 617225 reaction equation
Cl[CH2:2][C:3]1[C:12]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[C:11]([C:18]2[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[C:20]([O:26][CH3:27])[CH:19]=2)[C:10]2[C:5](=[CH:6][C:7]([O:30][CH3:31])=[C:8]([O:28][CH3:29])[CH:9]=2)[N:4]=1.[OH:32][C:33]1[CH:38]=[CH:37][CH:36]=[C:35]([CH3:39])[N:34]=1.C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>O>[CH3:27][O:26][C:20]1[CH:19]=[C:18]2[C:23](=[CH:22][C:21]=1[O:24][CH3:25])[N:4]=[C:3]([CH2:2][O:32][C:33]1[N:34]=[C:35]([CH3:39])[CH:36]=[CH:37][CH:38]=1)[C:12]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[C:11]2[C:10]1[CH:5]=[CH:6][C:7]([O:30][CH3:31])=[C:8]([O:28][CH3:29])[CH:9]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 10813243Ethyl 2-chloromethyl-4-(3,4-dimethoxyphenyl)-6,7-dimethoxyquinoline-3-carboxylateHCID 178425782HCID 178425782, compound

Product 1

HCID 21851171Ethyl 6,7-dimethoxy-4-(3,4-dimethoxyphenyl)-2-[(2-methyl-6-pyridyl)oxymethyl]quinoline-3-carboxylateYield 46%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of ethyl 2-chloromethyl-6,7-dimethoxy-4- (3,4-dimethoxyphenyl)quinoline-3-carboxylate (1.5 g), 2-hydroxy-6-methylpyridine (0.4 g), potassium carbonate (0.511 g) and N,N-dimethylformamide (20 ml) was stirred at 120° C. for 2 hours. Then the mixture was poured into water and extracted with ethyl acetate. The ethyl acetate layer was washed with water and dried (MgSO4), and the solvent was distilled off. The residual oil was subjected to column chromatography on silica gel. From the fraction eluted with ethyl acetate, ethyl 6,7-dimethoxy-4-(3,4-dimethoxyphenyl)- 2-[(2-methyl-6-pyridyl)oxymethyl]quinoline-3-carboxylate (0.79 g, 46%) was obtained and recrystallized from chloroform/hexane.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe ethyl acetate layer was washed with water
  3. dry with materialdried (MgSO4)
  4. distillationthe solvent was distilled off
  5. washFrom the fraction eluted with ethyl acetate

Sources & evidence

ORD record
ord-67eb78d45cdd4befbc99b63de0d24264
Source dataset
uspto-grants-1999_09
Patent number
US05948782

Reaction notes

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