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

HRID 83780Notes

Reaction equation

HRID 83780 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

2-(4-Acetylaminophenoxy)-propionic acid methyl ester 8 (320 g, 1.35 mol) in conc. HCl (8 L) was refluxed for 48 hours. Excess conc. HCl was distilled off in vacuum and filtered hot. The mixture was cooled to 10° C., filtered and dried to give pure 9 (240 g, 81.7%) as a brown powder with an m.p between 175-180° C.

Workup

  1. distillationExcess conc. HCl was distilled off in vacuum
  2. filtrationfiltered hot
  3. filtrationfiltered
  4. customdried

Sources & evidence

ORD record
ord-86196e2ea1f94f5e91762a46aaf07482
Source dataset
uspto-grants-2014_09
Patent number
US08846845B2

Reaction notes

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