Ethylene carbonate → 2,6-Dimethyl-3-methoxycarbonyl-4-(3-nitrophenyl)-5-(2-[4-(2-hydroxyethoxy)phenyl]ethoxycarbonyl)-1,4-dihydropyridine

HRID 652549Notes

Reaction equation

HRID 652549 reaction equation
[CH3:1][C:2]1[NH:3][C:4]([CH3:33])=[C:5]([C:21]([O:23][CH2:24][CH2:25][C:26]2[CH:31]=[CH:30][C:29]([OH:32])=[CH:28][CH:27]=2)=[O:22])[CH:6]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([N+:18]([O-:20])=[O:19])[CH:13]=2)[C:7]=1[C:8]([O:10][CH3:11])=[O:9].C([O-])([O-])=O.[K+].[K+].C1(=O)O[CH2:43][CH2:42][O:41]1>C1(C)C=CC=CC=1>[CH3:1][C:2]1[NH:3][C:4]([CH3:33])=[C:5]([C:21]([O:23][CH2:24][CH2:25][C:26]2[CH:27]=[CH:28][C:29]([O:32][CH2:43][CH2:42][OH:41])=[CH:30][CH:31]=2)=[O:22])[CH:6]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([N+:18]([O-:20])=[O:19])[CH:13]=2)[C:7]=1[C:8]([O:10][CH3:11])=[O:9]

Participants

5

Reactant 3

HCID 7303Ethylene carbonateHCID 11430Potassium CarbonateHCID 201974812,6-Dimethyl-3-methoxycarbonyl-4-(3-nitrophenyl)-5-[2-(4-hydroxyphenyl)ethoxycarbonyl]-1,4-dihydropyridine

Product 1

HCID 201976432,6-Dimethyl-3-methoxycarbonyl-4-(3-nitrophenyl)-5-(2-[4-(2-hydroxyethoxy)phenyl]ethoxycarbonyl)-1,4-dihydropyridineYield 91.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 1.0 g of 2,6-dimethyl-3-methoxycarbonyl-4-(3-nitrophenyl)-5-[2-(4-hydroxyphenyl)ethoxycarbonyl]-1,4-dihydropyridine (11), 0.5 g of K2CO3, and 0.5 g of ethylene carbonate in 20 mL of toluene was heated at reflux for 18 h. The mixture was filtered and the filtrate evaporated to yield 1.0 g of 2,6-dimethyl-3-methoxycarbonyl-4-(3-nitrophenyl)-5-(2-[4-(2-hydroxyethoxy)phenyl]ethoxycarbonyl)-1,4-dihydropyridine (1, R1 =A1, m=2, p=0) as an amorphous solid.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 18 h
  3. filtrationThe mixture was filtered
  4. customthe filtrate evaporated

Sources & evidence

ORD record
ord-bbffbd23e1a548b0995a4c12833c9d1e
Source dataset
uspto-grants-1987_06
Patent number
US04672071

Reaction notes

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