Hydrochloric Acid → 2-[[2-(3-chloro-4-prop-2-enoxyphenyl)acetyl]amino]acetic acid

HRID 1262535Notes

Reaction equation

HRID 1262535 reaction equation
C[O:2][C:3](=[O:20])[CH2:4][NH:5][C:6](=[O:19])[CH2:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][CH2:15][CH:16]=[CH2:17])=[C:10]([Cl:18])[CH:9]=1.[OH-].[Na+].Cl>CC(C)=O>[CH2:15]([O:14][C:11]1[CH:12]=[CH:13][C:8]([CH2:7][C:6]([NH:5][CH2:4][C:3]([OH:20])=[O:2])=[O:19])=[CH:9][C:10]=1[Cl:18])[CH:16]=[CH2:17]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 12796233HCID 12796233, compound

Product 1

HCID 5353122-[[2-(3-chloro-4-prop-2-enoxyphenyl)acetyl]amino]acetic acidYield 79.5%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
40 °C

Procedure

4-Allyloxy-3-chloro-phenylacetyl-glycine methyl ester (0.594 g) was suspended in acetone (8.0 ml) to which was added aqueous sodium hydroxide solution (1 M, 4.0 ml) and the whole was warmed to 40° C. for 30 min. After the solution had been cooled to 0° C., the pH was adjusted to 2-3 using dilute hydrochloric acid (3 M) and quickly extracted with ethyl acetate (20 ml). The extract was dried (anhydrous sodium sulphate). The solvent was evaporated at reduced pressure to leave a solid residue (450 mg), m.p. 115°-119° C. After recrystallisation from ethyl acetate/light petroleum (b.p. 60°-80° C.) the above-named product, m.p. 117°-119° C., was obtained.

Workup

  1. temperatureAfter the solution had been cooled to 0° C.
  2. extractionquickly extracted with ethyl acetate (20 ml)
  3. dry with materialThe extract was dried (anhydrous sodium sulphate)
  4. customThe solvent was evaporated at reduced pressure

Sources & evidence

ORD record
ord-1beb5959556e4e718074db2b303d8f6d
Source dataset
uspto-grants-1984_06
Patent number
US04452783

Reaction notes

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