Toluene → HCID 23332192, compound

HRID 224211Notes

Reaction equation

HRID 224211 reaction equation
C(C([CH:9]=[CH:10][C:11]([C:17]#[N:18])=[C:12](O)[C:13]([OH:15])=[O:14])=C(O)C(O)=O)#N.[Cl:19][C:20]1[CH:21]=[C:22]([CH:24]=[CH:25][CH:26]=1)[NH2:23].C1(C)C=CC=CC=1>O>[C:17]([C:11]1[CH:10]=[CH:9][N:23]([C:22]2[CH:24]=[CH:25][CH:26]=[C:20]([Cl:19])[CH:21]=2)[C:12]=1[C:13]([OH:15])=[O:14])#[N:18]

Participants

5

Reactant 3

HCID 1140TolueneHCID 79323-ChloroanilineHCID 86737280HCID 86737280, compound

Product 1

HCID 23332192HCID 23332192, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 9.2 g of the diethyl ester of 3,6-dicyano-2,7-dihydroxy-2,4,6-octatrienedioic acid (Huisgen and Laschtuvka, supra), 7.0 g of 3-chloroaniline and 75 ml of dry toluene was stirred at reflux for 3 hours, water of reaction being distilled from the mixture as it was formed. The resulting mixture was filtered and the solvent was evaporated under reduced pressure. The residue was dissolved in 35 ml of hot ethanol and the solution was chilled in a freezer. The resulting solid was filtered and dried under vacuum to give the ethyl ester of 3-cyano-1-(3-chlorophenyl)-1H-pyrrole-2-carboxylic acid (IA), m.p.: 113°-116° C.

Workup

  1. temperatureat reflux for 3 hours
  2. distillationbeing distilled from the mixture as it
  3. customwas formed
  4. filtrationThe resulting mixture was filtered
  5. customthe solvent was evaporated under reduced pressure
  6. dissolutionThe residue was dissolved in 35 ml of hot ethanol
  7. temperaturethe solution was chilled in a freezer
  8. filtrationThe resulting solid was filtered
  9. customdried under vacuum

Sources & evidence

ORD record
ord-94174990949a4c82a3e3f162bde3f6dd
Source dataset
uspto-grants-1980_11
Patent number
US04231785

Reaction notes

Loading…