Butanoic acid, 2-[(3-nitrophenyl)methylene]-3-oxo-, 1-methylethyl ester → 3-[2-[(E)-3-[4-(pyridin-3-ylmethyl)phenyl]-2-methylallyloxy]ethyl] 5-isopropyl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate

HRID 986456Notes

Reaction equation

HRID 986456 reaction equation
[NH2:1]/[C:2](/[CH3:27])=[CH:3]\[C:4]([O:6][CH2:7][CH2:8][O:9][CH2:10]/[C:11](/[CH3:26])=[CH:12]/[C:13]1[CH:18]=[CH:17][C:16]([CH2:19][C:20]2[CH:21]=[N:22][CH:23]=[CH:24][CH:25]=2)=[CH:15][CH:14]=1)=[O:5].[N+:28]([C:31]1[CH:32]=[C:33]([CH:45]=[CH:46][CH:47]=1)[CH:34]=[C:35]([C:42]([CH3:44])=O)[C:36]([O:38][CH:39]([CH3:41])[CH3:40])=[O:37])([O-:30])=[O:29]>C(O)(C)C>[CH3:27][C:2]1[NH:1][C:42]([CH3:44])=[C:35]([C:36]([O:38][CH:39]([CH3:41])[CH3:40])=[O:37])[CH:34]([C:33]2[CH:45]=[CH:46][CH:47]=[C:31]([N+:28]([O-:30])=[O:29])[CH:32]=2)[C:3]=1[C:4]([O:6][CH2:7][CH2:8][O:9][CH2:10]/[C:11](/[CH3:26])=[CH:12]/[C:13]1[CH:14]=[CH:15][C:16]([CH2:19][C:20]2[CH:21]=[N:22][CH:23]=[CH:24][CH:25]=2)=[CH:17][CH:18]=1)=[O:5]

Participants

4

Reactant 2

HCID 3951175Butanoic acid, 2-[(3-nitrophenyl)methylene]-3-oxo-, 1-methylethyl esterHCID 704156632-[(E)-3-[4-(pyridin-3-ylmethyl)phenyl]-2-methylallyloxy]ethyl 3-aminocrotonate

Product 1

HCID 140329463-[2-[(E)-3-[4-(pyridin-3-ylmethyl)phenyl]-2-methylallyloxy]ethyl] 5-isopropyl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylateYield 75.9%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

In 1.36 ml of isopropanol were dissolved 340 mg of 2-[(E)-3-[4-(pyridin-3-ylmethyl)phenyl]-2-methylallyloxy]ethyl 3-aminocrotonate and 257 mg of isopropyl 2-(3-nitrobenzylidene)acetoacetate, and the resulting solution was subjected to reaction under refulx for 2 hours. The reaction mixture was thereafter stirred with ice-cooling, and the crystals thus precipitated were collected by filtration to obtain 440 mg (yield 75.8%) of 3-[2-[(E)-3-[4-(pyridin-3-ylmethyl)phenyl]-2-methylallyloxy]ethyl] 5-isopropyl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate having a melting point of 124°-126° C. The physical properties of this product were identical with those of the compound obtained in Example 29.

Workup

  1. customthe resulting solution was subjected to reaction under refulx for 2 hours
  2. temperaturecooling
  3. customthe crystals thus precipitated
  4. filtrationwere collected by filtration

Sources & evidence

ORD record
ord-d54418f5259048659a38d1699cbc35c8
Source dataset
uspto-grants-1987_12
Patent number
US04713387

Reaction notes

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