Water → N-(3,4-dichlorophenyl)alanine

HRID 23019

Reaction equation

HRID 23019 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][C:8]=1[Cl:9])[NH2:5].O.Cl[CH:12]([CH3:16])[C:13]([OH:15])=[O:14].C(=O)(O)[O-].[Na+]>C(O)(C)C>[Cl:1][C:2]1[CH:3]=[C:4]([NH:5][C@H:12]([C:13]([OH:15])=[O:14])[CH3:16])[CH:6]=[CH:7][C:8]=1[Cl:9]

Participants

6

Reactant 4

HCID 962Water2×HCID 72573,4-DichloroanilineHCID 117342-Chloropropionic acidHCID 516892Sodium Bicarbonate

Product 1

HCID 5491659N-(3,4-dichlorophenyl)alanine

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
40 °C

Procedure

Using the procedure set forth in U.S. Pat. No. 3,598,859, the disclosure of which is incorporated herein by reference in its entirety. N-(3,4-dichlorophenyl)alanine was prepared. Specifically, to a solution of 3,4-dichloroaniline (1 equivalent) (Aldrich) in isopropanol (about 500 mL per mole of 3,4-dichloroaniline) is added water (about 0.06 mL per mL of isopropanol) and 2-chloropropionic acid (2 equivalents) (Aldrich). This mixture is warmed to 40° C. and sodium bicarbonate (0.25 equivalents) is added in successive portions before heating under reflux for 4-5 days. After cooling, the reaction mixture is poured into water and the unreacted 3,4-dichloroaniline is removed by filtration. The filtrate is acidified to pH 3-4 with concentrated hydrochloric acid and the resultant precipitate is filtered, washed and dried to yield the title compound, m.p.=148-149° C.

Workup

  1. customN-(3,4-dichlorophenyl)alanine was prepared
  2. temperaturebefore heating
  3. temperatureunder reflux for 4-5 days
  4. temperatureAfter cooling
  5. customthe unreacted 3,4-dichloroaniline is removed by filtration
  6. filtrationthe resultant precipitate is filtered
  7. washwashed
  8. customdried

Sources & evidence

ORD record
ord-01af6eabe3f04be4b905847b889fd958
Source dataset
uspto-grants-2005_02
Patent number
US06849650B2

Linked notes

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