Methyl 3-(dimethylamino)acrylate → Methyl 4-(2,3-dichlorophenyl)-1H-pyrrole-3-carboxylate

HRID 247628

Reaction equation

HRID 247628 reaction equation
Cl.[Cl:2][C:3]1[C:12]([Cl:13])=[CH:11][CH:10]=[CH:9][C:4]=1[C:5](=O)[CH2:6][NH2:7].CN(C)[CH:16]=[CH:17][C:18]([O:20][CH3:21])=[O:19].CC[O-].[Na+]>C(O)C>[C:18]([C:17]1[C:5]([C:4]2[CH:9]=[CH:10][CH:11]=[C:12]([Cl:13])[C:3]=2[Cl:2])=[CH:6][NH:7][CH:16]=1)([O:20][CH3:21])=[O:19]

Participants

5

Reactant 3

HCID 566587Methyl 3-(dimethylamino)acrylateHCID 2723922Sodium ethoxideHCID 22151845Ethanone, 2-amino-1-(2,3-dichlorophenyl)-, hydrochloride

Product 1

HCID 15087831Methyl 4-(2,3-dichlorophenyl)-1H-pyrrole-3-carboxylate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

10.7 g of 2,3-dichlorophenacylamine hydrochloride and 6 g of methyl 3-dimethylaminoacrylate are heated for 2 hours under reflux in 120 ml of ethanol. Then a solution of 4 g of sodium ethylate in 40 ml of ethanol is added dropwise and the reaction mixture is heated for another hour under reflux. The reaction mixture is then concentrated by evaporation and the oily residue is purified by column chromatography (silica gel; elution with a 3:1 mixture of toluene/ethyl acetate. Melting point: 205°-206° C.

Workup

  1. temperaturethe reaction mixture is heated for another hour
  2. temperatureunder reflux
  3. concentrationThe reaction mixture is then concentrated by evaporation
  4. customthe oily residue is purified by column chromatography (silica gel
  5. washelution
  6. additionwith a 3:1 mixture of toluene/ethyl acetate

Sources & evidence

ORD record
ord-750983bedfe549e1acd00975d504a47a
Source dataset
uspto-grants-1987_11
Patent number
US04709053

Linked notes

Loading…