2-(4-Acetylamino-phenoxy)-propionic acid methyl ester → 2-(4-Aminophenoxy)propanoic acid

HRID 2405178Notes

Reaction equation

HRID 2405178 reaction equation
C[O:2][C:3](=[O:17])[CH:4]([O:6][C:7]1[CH:12]=[CH:11][C:10]([NH:13]C(=O)C)=[CH:9][CH:8]=1)[CH3:5]>Cl>[NH2:13][C:10]1[CH:9]=[CH:8][C:7]([O:6][CH:4]([CH3:5])[C:3]([OH:17])=[O:2])=[CH:12][CH:11]=1

Participants

3

Reactant 1

HCID 549413982-(4-Acetylamino-phenoxy)-propionic acid methyl ester

Product 1

HCID 141969882-(4-Aminophenoxy)propanoic acidYield 98.1%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Conditions

Temperature
10 °C

Procedure

To a mixture 2-(4-acetylamino-phenoxy)-propionic acid methyl ester 62 (320 grams, 1.35 mol) in concentrated hydrochloric acid (8 liters) was refluxed for 48 hours. Excess concentrated hydrochloric acid was distilled in vacuum and filtered hot. The mixture was cooled to 10° C., filtered and dried to give pure 63 (240 grams, 81.7%) as a brown powder. The melting point was found to be 175-180° C.

Workup

  1. distillationExcess concentrated hydrochloric acid was distilled in vacuum
  2. filtrationfiltered hot
  3. filtrationfiltered
  4. customdried

Sources & evidence

ORD record
ord-1c238636c2eb482ab6055672df06a17a
Source dataset
uspto-grants-2014_08
Patent number
US08802892B2

Reaction notes

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