Hydrochloric Acid → 2-Amino-4-(2-nitrophenyl)butyric acid hydrochloride

HRID 482728Notes

Reaction equation

HRID 482728 reaction equation
C([NH:4][C:5]([CH2:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[N+:24]([O-:26])=[O:25])(C(OCC)=O)[C:6]([O:8]CC)=[O:7])(=O)C.[ClH:27]>>[ClH:27].[NH2:4][CH:5]([CH2:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[N+:24]([O-:26])=[O:25])[C:6]([OH:8])=[O:7]

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 20244794Diethyl acetamido[2-(2-nitrophenyl)ethyl]propanedioate

Product 1

HCID 132435492-Amino-4-(2-nitrophenyl)butyric acid hydrochloride

Procedure

A solution of diethyl 2-acetamido-2-(o-nitrophenethyl)malonate (80 g) in 3N hydrochloric acid (900 ml) was refluxed for 12 hours. The solution was cooled and extracted with ethyl acetate (200 ml). The aqueous solution was filtered, and evaporated to dryness under reduced pressure. The residue was recrystallized from ethanol/ether to give 2-amino-4-(2-nitrophenyl)butyric acid hydrochloride, m.p. 219°-221° (dec).

Workup

  1. temperatureThe solution was cooled
  2. extractionextracted with ethyl acetate (200 ml)
  3. filtrationThe aqueous solution was filtered
  4. customevaporated to dryness under reduced pressure
  5. customThe residue was recrystallized from ethanol/ether

Sources & evidence

ORD record
ord-03de7b5911b949918e4c6b67b32900a3
Source dataset
uspto-grants-1986_03
Patent number
US04575503

Reaction notes

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