Diethylamine → HCID 20533149, compound

HRID 1248717Notes

Reaction equation

HRID 1248717 reaction equation
[CH3:1][C:2]1[NH:3][C:4]([CH:28]([O:32][CH2:33][CH3:34])[O:29][CH2:30][CH3:31])=[C:5]([C:23]([O:25][CH2:26][CH3:27])=[O:24])[CH:6]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([N+:20]([O-:22])=[O:21])[CH:15]=2)[C:7]=1[C:8]([O:10][CH2:11][CH2:12]Cl)=[O:9].[CH2:35]([NH:37][CH2:38][CH3:39])[CH3:36]>C(O)CC.[I-].[Na+]>[CH3:1][C:2]1[NH:3][C:4]([CH:28]([O:32][CH2:33][CH3:34])[O:29][CH2:30][CH3:31])=[C:5]([C:23]([O:25][CH2:26][CH3:27])=[O:24])[CH:6]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([N+:20]([O-:22])=[O:21])[CH:15]=2)[C:7]=1[C:8]([O:10][CH2:11][CH2:12][N:37]([CH2:38][CH3:39])[CH2:35][CH3:36])=[O:9]

Participants

5

Reactant 2

HCID 8021DiethylamineHCID 13469481HCID 13469481, compound

Product 1

HCID 20533149HCID 20533149, compoundYield 19.3%

Reagents, catalysts & solvents 2

HCID 5238Sodium IodideCatalystHCID 10311-PropanolSolvent

Procedure

A mixture of 2-chloroethyl 2-methyl-4-(3-nitrophenyl)-5-ethoxycarbonyl-6-diethoxymethyl-1,4-dihydropyridine-3-carboxylate (20 g), diethylamine (1.75 g) and sodium iodide (60.3 mg) in n-propylalcohol (4 ml) was refluxed for 17 hours. After removal of the solvent from the reaction mixture, water and ethyl acetate were added to the residue. The ethyl acetate layer was washed twice with water, dried over magnesium sulfate, and concentrated to give a brown oil (2.46 g) of 2-(N,N-diethylamino)ethyl 2-methyl-4-(3-nitrophenyl)-5-ethoxycarbonyl-6-diethoxymethyl-1,4-dihydropyridine-3-carboxylate, which was identified by converting to the corresponding 6-formyl compound (oil) and then to the corresponding 6-cyano compound, m.p. 150° to 152° C.

Workup

  1. temperaturewas refluxed for 17 hours
  2. customAfter removal of the solvent from the reaction mixture, water and ethyl acetate
  3. additionwere added to the residue
  4. washThe ethyl acetate layer was washed twice with water
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-91ac9ad53b324a66afab07fcf7509d08
Source dataset
uspto-grants-1985_06
Patent number
US04525478

Reaction notes

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