2-Butenoic acid, 3-amino-, ethyl ester, (2Z)- → 1,4-Dihydro-2,6-dimethyl-4-(2-methylbenzo[b]thien-3-yl)-3,5-pyridinedicarboxylic acid, diethyl ester

HRID 542774

Reaction equation

HRID 542774 reaction equation
[CH3:1][C:2]1[S:6][C:5]2[CH:7]=[CH:8][CH:9]=[CH:10][C:4]=2[C:3]=1[CH:11]=O.[NH2:13]/[C:14](/[CH3:21])=[CH:15]\[C:16]([O:18][CH2:19][CH3:20])=[O:17]>C(O)C>[CH3:21][C:14]1[NH:13][C:14]([CH3:21])=[C:15]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH:11]([C:3]2[C:4]3[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=3[S:6][C:2]=2[CH3:1])[C:15]=1[C:16]([O:18][CH2:19][CH3:20])=[O:17]

Participants

4

Reactant 2

HCID 6437562-Butenoic acid, 3-amino-, ethyl ester, (2Z)-2×HCID 37754672-Methyl-1-benzothiophene-3-carbaldehyde

Product 1

HCID 138268541,4-Dihydro-2,6-dimethyl-4-(2-methylbenzo[b]thien-3-yl)-3,5-pyridinedicarboxylic acid, diethyl esterYield 43.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2.2 g of 2-methylbenzo[b]thiophene-3-carboxaldehyde, 4.9 g of ethyl 3-aminocrotonate, and 10 ml of ethanol were heated to reflux for approximately 18 hours. An additional 1.6 g of ethyl 3-aminocrotonate were added and the reaction was heated an additional 24 hours at reflux. The reaction mixture was cooled and concentrated and the resulting solid was recovered by filtration providing 2.15 g of the desired title product, m.p. 191°-193° C.

Workup

  1. temperaturewere heated
  2. temperatureto reflux for approximately 18 hours
  3. temperaturethe reaction was heated an additional 24 hours
  4. temperatureat reflux
  5. temperatureThe reaction mixture was cooled
  6. concentrationconcentrated
  7. filtrationthe resulting solid was recovered by filtration

Sources & evidence

ORD record
ord-1d3dcd6e82f24cff84d6d8aa644653d9
Source dataset
uspto-grants-1987_04
Patent number
US04659717

Linked notes

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