Water → 4-Amino-5-chloro-2-(2-methoxyethoxy)benzoic acid

HRID 5372

Reaction equation

HRID 5372 reaction equation
C[O:2][C:3](=[O:17])[C:4]1[CH:9]=[C:8]([Cl:10])[C:7]([NH2:11])=[CH:6][C:5]=1[O:12][CH2:13][CH2:14][O:15][CH3:16].[OH-].[Na+].O>C(O)C>[NH2:11][C:7]1[C:8]([Cl:10])=[CH:9][C:4]([C:3]([OH:17])=[O:2])=[C:5]([O:12][CH2:13][CH2:14][O:15][CH3:16])[CH:6]=1

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 539320764-Amino-5-chloro-2-(2-methoxyethoxy)benzoic acid methyl ester

Product 1

HCID 197959774-Amino-5-chloro-2-(2-methoxyethoxy)benzoic acidYield 78%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 4-amino-5-chloro-2-(2-methoxyethoxy)benzoic acid methyl ester (2.75 g, 10.6 mmol) in 95% ethanol (20 mL) was treated with 50% sodium hydroxide (10 mL) and water (10 mL), and refluxed for one hour. The ethanol was removed in vacuo and replaced with water. The aqueous solution was extracted with ether (20 mL) and acidified to pH 4 with concentrated hydrochloric acid (16 mL). A solid soon precipitated, and this was filtered, washed with water, air dried, and recrystallized from ethyl acetate (2 crops) to afford 2.03 g (75%) of fine pale tan needles; mp 119°-120° C.

Workup

  1. temperaturerefluxed for one hour
  2. customThe ethanol was removed in vacuo
  3. extractionThe aqueous solution was extracted with ether (20 mL)
  4. customA solid soon precipitated
  5. filtrationthis was filtered
  6. washwashed with water, air
  7. customdried
  8. customrecrystallized from ethyl acetate (2 crops)

Sources & evidence

ORD record
ord-1be6548ad9b94f2f8afd6c1d75cd9889
Source dataset
uspto-grants-1993_09
Patent number
US05244907

Linked notes

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