Ethylene Glycol → Diethyl 2-methyl-4-(2-nitrophenyl)-6-ethylenedioxymethyl-1,4-dihydropyridine-3,5-dicarboxylate

HRID 894702Notes

Reaction equation

HRID 894702 reaction equation
C[C:2]1[NH:3][C:4]([CH:27]=O)=[C:5]([C:22]([O:24][CH2:25][CH3:26])=[O:23])[CH:6]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[N+:19]([O-:21])=[O:20])[C:7]=1[C:8]([O:10][CH2:11][CH3:12])=[O:9].[CH2:29]([OH:32])[CH2:30][OH:31].[C:33]1(C)C=CC(S(O)(=O)=O)=CC=1>C1C=CC=CC=1>[CH3:27][C:4]1[N:3]2[O:32][CH2:29][CH2:30][O:31][C:2]2=[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[C:6]([CH3:33])([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[N+:19]([O-:21])=[O:20])[C:5]=1[C:22]([O:24][CH2:25][CH3:26])=[O:23]

Participants

5

Reactant 3

HCID 174Ethylene GlycolHCID 6101p-Toluenesulfonic acidHCID 13388352Diethyl 2-methyl-4-(2-nitrophenyl)-6-formyl-1,4-dihydropyridine-3,5-dicarboxylate

Product 1

HCID 70071585Diethyl 2-methyl-4-(2-nitrophenyl)-6-ethylenedioxymethyl-1,4-dihydropyridine-3,5-dicarboxylate

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture of diethyl 2-methyl-4-(2-nitrophenyl)-6-formyl-1,4-dihydropyridine-3,5-dicarboxylate (388.37 mg), ethylene glycol (186.21 mg) and p-toluenesulfonic acid (catalytic amount) in absolute benzene (5 ml) was refluxed for 45 minutes under azeotropic dehydration. The reaction mixture was allowed to stand and washed twice with an aqueous solution of sodium bicarbonate. After removal of the solvent, the residue immediately turned into crystals. Thus obtained crystals were recrystallized from a mixture of ethanol and diisopropyl ether to give yellow pure crystals (0.32 g) of diethyl 2-methyl-4-(2-nitrophenyl)-6-ethylenedioxymethyl-1,4-dihydropyridine-3,5-dicarboxylate, m.p. 152° to 153.5° C.

Workup

  1. temperaturewas refluxed for 45 minutes under azeotropic dehydration
  2. washwashed twice with an aqueous solution of sodium bicarbonate
  3. customAfter removal of the solvent
  4. customThus obtained crystals were recrystallized from a mixture of ethanol and diisopropyl ether

Sources & evidence

ORD record
ord-b63192aa557944c3ba9869d6824af63a
Source dataset
uspto-grants-1981_08
Patent number
US04284634

Reaction notes

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