Hydrochloric Acid → HCID 14835691, compound

HRID 1709248Notes

Reaction equation

HRID 1709248 reaction equation
[CH:1]([C:4]1[CH:9]=[CH:8][C:7](/[CH:10]=[CH:11]/[C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:6][C:5]=1[N+:17]([O-])=O)([CH3:3])[CH3:2].Cl.C(=O)([O-])O.[Na+]>C(O)C.[Fe]>[NH2:17][C:5]1[CH:6]=[C:7](/[CH:10]=[CH:11]/[C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH:8]=[CH:9][C:4]=1[CH:1]([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium Bicarbonate2×HCID 14835686HCID 14835686, compound

Product 1

HCID 14835691HCID 14835691, compoundYield 85.5%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 702EthanolSolvent

Procedure

13.2 g of ethyl (E)-3-(4-isopropyl-3-nitrophenyl)acrylate was dissolved in 330 ml of 80% ethanol. Thereto were added 27.9 g of an iron powder and 4.17 ml of concentrated hydrochloric acid at room temperature. The mixture was refluxed for 1.5 hours. The reaction mixture was neutralized with sodium hydrogencarbonate. The resulting insolubles were removed by filtration and the filtrate was subjected to distillation under reduced pressure to remove the solvent. To the residue were added 100 ml of water and 200 ml of diethyl ether. The mixture was adjusted to pH 1.0 with concentrated hydrochloric acid. The resulting crystals were filtered. The crystals obtained and the separated aqueous layer obtained from the filtrate were combined and neutralized with sodium hydrogencarbonate. Then, the mixture was extracted with ethyl acetate. The extract was washed with water and a saturated aqueous sodium chloride solution in this order and dried over anhydrous magnesium sulfate. The solvent was removed by distillation under reduced pressure to obtain 10.0 g of brown oily ethyl (E)-3-(3-amino- 4-isopropylphenyl)acrylate.

Workup

  1. temperatureThe mixture was refluxed for 1.5 hours
  2. customThe resulting insolubles were removed by filtration
  3. distillationthe filtrate was subjected to distillation under reduced pressure
  4. customto remove the solvent
  5. additionTo the residue were added 100 ml of water and 200 ml of diethyl ether
  6. filtrationThe resulting crystals were filtered
  7. customThe crystals obtained
  8. customthe separated aqueous layer obtained from the filtrate
  9. extractionThen, the mixture was extracted with ethyl acetate
  10. washThe extract was washed with water
  11. dry with materiala saturated aqueous sodium chloride solution in this order and dried over anhydrous magnesium sulfate
  12. customThe solvent was removed by distillation under reduced pressure

Sources & evidence

ORD record
ord-ad0b891abe1440f78e1de93896f8e644
Source dataset
uspto-grants-1990_08
Patent number
US04948796

Reaction notes

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