Hydrochloric Acid → 2-Propenoic acid, 3-(2-aminophenyl)-, ethyl ester, (2E)-

HRID 1197083Notes

Reaction equation

HRID 1197083 reaction equation
Cl.O.[N+:3]([C:6]1[CH:18]=[CH:17][CH:16]=[CH:15][C:7]=1[CH:8]=[CH:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])([O-])=O>C(O)C>[NH2:3][C:6]1[CH:18]=[CH:17][CH:16]=[CH:15][C:7]=1[CH:8]=[CH:9][C:10]([O:12][CH2:13][CH3:14])=[O:11]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 235998Ethyl 3-(2-nitrophenyl)prop-2-enoate

Product 1

HCID 27490502-Propenoic acid, 3-(2-aminophenyl)-, ethyl ester, (2E)-Yield 84.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2.2 g of reduced iron, 0.5 ml of conc. hydrochloric acid and 2.5 ml of water was added to a solution of 2.2 g of ethyl o-nitrocinnamate in 30 ml of ethanol. After heating under reflux for 1 hour, insoluble matters were filtered off and the filtrate was concentrated under reduced pressure. An aqueous sodium hydrogen carbonate solution was added to the residue followed by extraction with toluene. After the extract was washed with water and dried, the solvent was distilled off to obtain 1.6 g of ethyl o-aminocinnamate as yellow crystals.

Workup

  1. temperatureAfter heating
  2. temperatureunder reflux for 1 hour
  3. filtrationinsoluble matters were filtered off
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. additionAn aqueous sodium hydrogen carbonate solution was added to the residue
  6. extractionfollowed by extraction with toluene
  7. washAfter the extract was washed with water
  8. customdried
  9. distillationthe solvent was distilled off

Sources & evidence

ORD record
ord-c81078edda544665aab5d5be7d958f1c
Source dataset
uspto-grants-1992_05
Patent number
US05116853

Reaction notes

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