Hydrochloric Acid → HCID 14090769, compound

HRID 893848Notes

Reaction equation

HRID 893848 reaction equation
O.Cl.[CH2:3]([O:5][C:6](=[O:21])[CH:7]([N+:18]([O-])=O)[CH2:8][C:9]1[C:10]2[CH:17]=[CH:16][CH:15]=[CH:14][C:11]=2[S:12][CH:13]=1)[CH3:4]>[Fe].C(O)C>[CH2:3]([O:5][C:6](=[O:21])[CH:7]([NH2:18])[CH2:8][C:9]1[C:10]2[CH:17]=[CH:16][CH:15]=[CH:14][C:11]=2[S:12][CH:13]=1)[CH3:4]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 14994411HCID 14994411, compound

Product 1

HCID 14090769HCID 14090769, compoundYield 45.8%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 702EthanolSolvent

Procedure

To a mixed solution of 7.5 ml of water, 7.5 ml of ethanol, and 10 ml of 12N hydrochloric acid were added 3.5 g of iron powder and 2.79 g of 3-(benzo[b]thiophen-3-yl)-2-nitropropionic acid ethyl ester and then the reaction was carried out for one hour at room temperature. After filtered away excess iron powder, 200 ml of water was added to the filtrate and after adjusting the pH thereof to from 9 to 10 with sodium hydrogencarbonate, the mixture was extracted thrice with 50 ml of chloroform. The chloroform layer was washed twice with 200 ml of water and then twice with 100 ml of a saturated aqueous sodium chloride solution and after drying with magnesium sulfate, chloroform was distilled off under reduced pressure. The residue was dissolved in ethyl acetate, 10 ml of a solution composed of 1N hydrochloric acid and ethyl acetate, and crystals thus deposited were collected by filtration to provide 1.14 g (yield of 40%) of 2-amino-3-(benzo[b]thiophen-3-yl)propionic acid ethyl ester.

Workup

  1. filtrationAfter filtered away excess iron powder, 200 ml of water
  2. additionwas added to the filtrate
  3. extractionto from 9 to 10 with sodium hydrogencarbonate, the mixture was extracted thrice with 50 ml of chloroform
  4. washThe chloroform layer was washed twice with 200 ml of water
  5. dry with materialtwice with 100 ml of a saturated aqueous sodium chloride solution and after drying with magnesium sulfate, chloroform
  6. distillationwas distilled off under reduced pressure
  7. dissolutionThe residue was dissolved in ethyl acetate
  8. filtrationthus deposited were collected by filtration

Sources & evidence

ORD record
ord-51a88e10a0184b92aadf0445a6c73da2
Source dataset
uspto-grants-1992_06
Patent number
US05126448

Reaction notes

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