1,2-Dimethoxyethane → HCID 19772294, compound

HRID 1614669Notes

Reaction equation

HRID 1614669 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4](/[CH:8]=[CH:9]/[C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([CH2:16][O:17][CH2:18][CH2:19][CH2:20][CH2:21][C:22]3[CH:27]=[CH:26][C:25]([CH3:28])=[CH:24][CH:23]=3)[N:11]=2)[CH:5]=[CH:6][CH:7]=1.[C:29]([O:38]CC)(=O)[CH2:30][CH2:31][C:32]([O:34]CC)=[O:33].[C:41]([O-])(=O)[CH3:42].[Na+].[CH2:46]([CH2:49]OC)OC>>[C:32]([C:31]([CH2:41][CH3:42])([CH2:46][CH3:49])[CH2:30][C:29]([NH:1][C:2]1[CH:3]=[C:4](/[CH:8]=[CH:9]/[C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([CH2:16][O:17][CH2:18][CH2:19][CH2:20][CH2:21][C:22]3[CH:27]=[CH:26][C:25]([CH3:28])=[CH:24][CH:23]=3)[N:11]=2)[CH:5]=[CH:6][CH:7]=1)=[O:38])([OH:34])=[O:33]

Participants

5

Reactant 4

HCID 80711,2-DimethoxyethaneHCID 31249Diethyl SuccinateHCID 517045Sodium AcetateHCID 19772209HCID 19772209, compound

Product 1

HCID 19772294HCID 19772294, compound

Procedure

A solution of 1.25 g of 2-[(E)-2-(3-aminophenyl)ethenyl]-6-[4-(4-methylphenyl)butoxy]methylpyridine, 1.05 g of anhydrous diethyl succinate, 0.6 g of sodium acetate and 10 ml of dimethoxyethane was stirred under reflux for 5 hours. After completion of the reaction, the solvent was distilled off and to the residue was added water. After extracting with ethyl acetate, the organic layer was dried over anhydrous magnesium sulfate and the solvent was distilled off. To the residue was added isopropyl ether, the precipitated crystals were collected by filtration and recrystallized from ethanol to give 0.63 g of 2-[(E)-2-(3-(3-carboxy-3-ethylvalerylamino)phenyl)ethenyl]-6-[4-(4-methylphenyl)butoxy]methylpyridine, melting at 141°-142° C. as white crystals.

Workup

  1. temperatureunder reflux for 5 hours
  2. customAfter completion of the reaction
  3. distillationthe solvent was distilled off and to the residue
  4. additionwas added water
  5. extractionAfter extracting with ethyl acetate
  6. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  7. distillationthe solvent was distilled off
  8. additionTo the residue was added isopropyl ether
  9. filtrationthe precipitated crystals were collected by filtration
  10. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-d147dd7488a54e9eb6515a2917e0deb5
Source dataset
uspto-grants-1993_03
Patent number
US05198452

Reaction notes

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