Hydrochloric Acid → HCID 47002213, compound

HRID 1607391Notes

Reaction equation

HRID 1607391 reaction equation
[CH2:1]([O:3][C:4](=[O:15])[C:5]([C:13]#[N:14])=[CH:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[CH3:2].[ClH:16]>C(O)C.[Pt]=O>[ClH:16].[CH2:1]([O:3][C:4](=[O:15])[CH:5]([CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[CH2:13][NH2:14])[CH3:2]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 74845Ethyl benzylidenecyanoacetate

Product 1

HCID 47002213HCID 47002213, compound

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 702EthanolSolvent

Procedure

A solution of 1.01 g of 2-cyano-3-phenylpropenoic acid ethyl ester and 0.7 ml of concentrated hydrochloric acid in 20 ml of ethanol was hydrogenated over 0.1 g of platinum oxide under a hydrogen atmosphere at room temperature for 5 hours. After filtration of the catalyst, the filtrate was concentrated under reduced pressure. The residue was dissolved in water, washed with benzene, and then made alkaline by adding a 5% aqueous sodium bicarbonate solution. The alkaline solution was extracted with diethyl ether, the ethereal layer was washed with water and dried over anhydrous magnesium sulfate. Hydrogen chloride gas was passed into the ethereal solution. The ethereal solution was concentrated under reduced pressure to obtain 832 mg of 3-amino-2-benzylpropionic acid ethyl ester hydrochloride as colorless crystals.

Workup

  1. filtrationAfter filtration of the catalyst
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. dissolutionThe residue was dissolved in water
  4. washwashed with benzene
  5. additionby adding a 5% aqueous sodium bicarbonate solution
  6. extractionThe alkaline solution was extracted with diethyl ether
  7. washthe ethereal layer was washed with water
  8. dry with materialdried over anhydrous magnesium sulfate
  9. concentrationThe ethereal solution was concentrated under reduced pressure

Sources & evidence

ORD record
ord-1f7c4d54041846f8a0342be3b1cdb6a3
Source dataset
uspto-grants-1989_09
Patent number
US04863904

Reaction notes

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