Hydrochloric Acid → 2-(3,4-Dichloro-phenylamino)-propionic Acid

HRID 1096190Notes

Reaction equation

HRID 1096190 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[C:4]([Cl:9])[CH:3]=1.[NH2:10][C@H:11]([C:13]([OH:15])=[O:14])[CH3:12].CN(C)CCO.Cl>O>[Cl:9][C:4]1[CH:3]=[C:2]([NH:10][CH:11]([CH3:12])[C:13]([OH:15])=[O:14])[CH:7]=[CH:6][C:5]=1[Cl:8]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 5950L-AlanineHCID 79022-(Dimethylamino)ethanolHCID 290134-Bromo-1,2-dichlorobenzene

Product 1

HCID 69164262-(3,4-Dichloro-phenylamino)-propionic AcidYield 53%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 1-bromo-3,4-dichlorobenzene (5.10 g, 22.1 mmol), L-alanine (2.96 g, 33.2 mmol) copper(I) iodide (421 mg, 2.21 mmol), tri-potassium phosphate n-hydrate (15.3 g, 66.4 mmol), 2-(dimethylamino)ethanol (5.92 g, 66.4 mmol), and water (22 mL) was heated at 90° C. for 40 h, then poured onto ice water. The pH was set to 6 with 25% aq. HCl solution, and the mixture was extracted with EtOAc. The aqueous phase was acidified to pH 4.5 and extracted with EtOAc. The combined organic layers were dried (MgSO4), filtered, and evaporated. Chromatography (SiO2; EtOAc) afforded the title compound (2.71 g, 53%) as a 60:40 mixture of the (S) and (R) stereoisomers. Light brown solid, MS: 232.1 (M−H)−.

Workup

  1. additionpoured onto ice water
  2. extractionthe mixture was extracted with EtOAc
  3. extractionextracted with EtOAc
  4. dry with materialThe combined organic layers were dried (MgSO4)
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-a5572e7b485c4f0883285722f5f854f1
Source dataset
uspto-grants-2012_03
Patent number
US08138175B2

Reaction notes

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