2-Butenoic acid, 3-amino-, 1-methylethyl ester → 4-(2-Cyanophenyl)-5-methoxycarbonyl-6-dimethoxymethyl-2-methyl-1,4-dihydropyridine-3-carboxylic acid

HRID 1164648Notes

Reaction equation

HRID 1164648 reaction equation
[C:1]([C:3]1[CH:21]=[CH:20][CH:19]=[CH:18][C:4]=1[CH:5]=[C:6]([C:11]([CH:13]([O:16][CH3:17])[O:14][CH3:15])=O)[C:7]([O:9][CH3:10])=[O:8])#[N:2].[NH2:22]/[C:23](/[CH3:31])=[CH:24]\[C:25]([O:27]C(C)C)=[O:26]>C(OCC)(=O)C>[C:1]([C:3]1[CH:21]=[CH:20][CH:19]=[CH:18][C:4]=1[CH:5]1[C:6]([C:7]([O:9][CH3:10])=[O:8])=[C:11]([CH:13]([O:16][CH3:17])[O:14][CH3:15])[NH:22][C:23]([CH3:31])=[C:24]1[C:25]([OH:27])=[O:26])#[N:2]

Participants

4

Reactant 2

HCID 111372742-Butenoic acid, 3-amino-, 1-methylethyl esterHCID 53675930Methyl 2-(2-cyanobenzylidene)-4,4-dimethoxyacetoacetate

Product 1

HCID 202772614-(2-Cyanophenyl)-5-methoxycarbonyl-6-dimethoxymethyl-2-methyl-1,4-dihydropyridine-3-carboxylic acidYield 68.9%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of methyl 2-(2-cyanobenzylidene)-4,4-dimethoxyacetoacetate (10.1 g) and isopropyl 3-aminocrotonate (5.51 g) was heated for 40 minutes at 78° C. and for 5.5 hours at 120° C. with stirring, followed by heating for an hour at 125° C. without the stirring. After the reaction mixture was allowed to stand overnight, it was dissolved in ethyl acetate. This solution was washed twice with water, dried and then evaporated to dryness under reduced pressure to give a residue, which was crystallized from ethyl ether. The crystals were collected by filtration and washed with a small amount of ethyl ether to give crude powder of isopropyl ester of 4-(2-cyanophenyl)-5-methoxycarbonyl-6-dimethoxymethyl-2-methyl-1,4-dihydropyridine-3-carboxylic acid (8.96 g). Further, the crude product (0.77 g) was recovered from the filtrate. 0.5 g Of this crude product was recrystallized from isopropyl ether to give purified white powder of the same product (0.37 g), mp 171°-172.5° C.

Workup

  1. temperatureby heating for an hour at 125° C. without the stirring
  2. washThis solution was washed twice with water
  3. customdried
  4. customevaporated to dryness under reduced pressure
  5. customto give a residue, which
  6. customwas crystallized from ethyl ether
  7. filtrationThe crystals were collected by filtration
  8. washwashed with a small amount of ethyl ether

Sources & evidence

ORD record
ord-1f54b043ebaa4fc68d5b5686f7003145
Source dataset
uspto-grants-1983_01
Patent number
US04370334

Reaction notes

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