Dicyclohexylcarbodiimide → Ethyl 5-phenyl-2,4-pentadienyl 4-(3-nitrophenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate

HRID 652424Notes

Reaction equation

HRID 652424 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:10]2[C:15]([C:16](O)=[O:17])=[C:14]([CH3:19])[NH:13][C:12]([CH3:20])=[C:11]2[C:21]([O:23][CH2:24][CH3:25])=[O:22])[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].C1(N=C=NC2CCCCC2)CCCCC1.[C:41]1([CH:47]=[CH:48][CH:49]=[CH:50][CH2:51][OH:52])[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1>CN(C)C1C=CN=CC=1.ClC(Cl)C>[N+:1]([C:4]1[CH:5]=[C:6]([CH:10]2[C:15]([C:16]([O:52][CH2:51][CH:50]=[CH:49][CH:48]=[CH:47][C:41]3[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=3)=[O:17])=[C:14]([CH3:19])[NH:13][C:12]([CH3:20])=[C:11]2[C:21]([O:23][CH2:24][CH3:25])=[O:22])[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2]

Participants

6

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 46567273-Ethyl 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylateHCID 534270135-Phenyl-2,4-Pentadienol

Product 1

HCID 86741577Ethyl 5-phenyl-2,4-pentadienyl 4-(3-nitrophenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylateYield 93%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 63651,1-DichloroethaneSolvent

Procedure

346 mg (1 mM) of 4-(3-nitrophenyl)-2,6-dimethyl-3-ethoxycarbonyl-1,4-dihydropyridine-5-carboxylic acid, 226 mg (1.1 mM) of dicyclohexylcarbodiimide, 122 mg (1 mM) of 4-dimethylaminopyridine and 192 mg (1.2 mM) of 5phenyl-2,4-pentadien-1-ol were dissolved in 10 ml of dichloroethane, and refluxed for 2 hours. Thereafter, the reaction mixture was treated in the same manner as Example 48, and 454 mg of ethyl 5-phenyl-2,4-pentadienyl 4-(3-nitrophenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate was obtained (yield 93%).

Workup

  1. temperaturerefluxed for 2 hours
  2. additionThereafter, the reaction mixture was treated in the same manner as Example 48

Sources & evidence

ORD record
ord-1c2fc9f493374c9fbed4778d488b1430
Source dataset
uspto-grants-1987_06
Patent number
US04672068

Reaction notes

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