Ethanol → HCID 86743133, compound

HRID 1904579Notes

Reaction equation

HRID 1904579 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:10]=[C:11]([C:17](=[O:20])[CH2:18][Cl:19])[C:12]([O:14][CH2:15]C)=[O:13])[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].[NH2:21]/[C:22](/[CH3:28])=[CH:23]\[C:24]([O:26][CH3:27])=[O:25].[CH3:29]CO>>[NH2:21][C:22](=[C:23]([C:24]([O:26][CH2:27][CH3:29])=[O:25])[CH:10]([C:6]1[CH:7]=[CH:8][CH:9]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=1)[CH:11]([C:12]([O:14][CH3:15])=[O:13])[C:17](=[O:20])[CH2:18][Cl:19])[CH3:28]

Participants

4

Reactant 3

HCID 702EthanolHCID 643918Methyl 3-aminocrotonateHCID 54565674HCID 54565674, compound

Product 1

HCID 86743133HCID 86743133, compound

Procedure

A mixture of ethyl 2-(m-nitrophenylmethylene)-4-chloro-3-oxobutanoate (80 g) and methyl 3-aminocrotonate (32.7 g) in EtOH (800 ml) is heated to reflux temperature for 15 minutes, then, without isolating the formed intermediate, 2-amino-7-chloro-3-carboethoxy-5-carbomethoxy-4-(m-nitrophenyl)-6-oxo-2-heptene, the mixture is cooled at 0° C. and acidified with aqueous concentrated HCl (3 ml). After two hours the reaction mixture is neutralized with a few drops of a saturated NaHCO3 solution and evaporated to dryness. The residue is dissolved in AcOEt (400 ml), washed with water (4×50 ml), dried on Na2SO4 and concentrated in vacuum. The residue is dissolved in Et2O to give 80 g of 2-chloromethyl-3-carboethoxy-5-carbomethoxy-4-(m-nitrophenyl)-6-methyl-1,4-dihydropyridine (m.p. 119°-120° C.).

Workup

  1. temperatureis heated
  2. temperatureto reflux temperature for 15 minutes

Sources & evidence

ORD record
ord-49f566f46d00439b94265c13ee285091
Source dataset
uspto-grants-1989_06
Patent number
US04839348

Reaction notes

Loading…