Diethyl 2-(2-(hydroxy(oxido)amino)benzyl)malonate → 3-(2-Nitrophenyl)propionic acid

HRID 1434554Notes

Reaction equation

HRID 1434554 reaction equation
[N+:1]([C:4]1[CH:21]=[CH:20][CH:19]=[CH:18][C:5]=1[CH2:6][CH:7](C(OCC)=O)[C:8]([O:10]CC)=[O:9])([O-:3])=[O:2]>Cl.C(O)(=O)C>[N+:1]([C:4]1[CH:21]=[CH:20][CH:19]=[CH:18][C:5]=1[CH2:6][CH2:7][C:8]([OH:10])=[O:9])([O-:3])=[O:2]

Participants

4

Reactant 1

HCID 309274Diethyl 2-(2-(hydroxy(oxido)amino)benzyl)malonate

Product 1

HCID 748183-(2-Nitrophenyl)propionic acid

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 313Hydrochloric AcidSolvent

Procedure

A solution of crude diethyl (2-nitrobenzyl)malonate in 6N aqueous HCl (15 ml) and acetic acid (15 ml) was stirred at refluxing temperature for 48 hours. After cooled to ambient temperature, the mixture was concentrated under reduced pressure. To the residue was added 10% aqueous NaOH solution and washed with ethyl acetate. The aqueous layer was acidified with aqueous HCl solution, and the mixture was extracted with ethyl acetate. The organic layer was dried over MgSO4, filtered, and concentrated under reduced pressure to obtain 3-(2-nitrophenyl)propanoic acid.

Workup

  1. temperatureat refluxing temperature for 48 hours
  2. concentrationthe mixture was concentrated under reduced pressure
  3. additionTo the residue was added 10% aqueous NaOH solution
  4. washwashed with ethyl acetate
  5. extractionthe mixture was extracted with ethyl acetate
  6. dry with materialThe organic layer was dried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-70ca1853bf354d4896b29fe5d12fa8d9
Source dataset
uspto-grants-2009_11
Patent number
US07615557B2

Reaction notes

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