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

HRID 846601

Reaction equation

HRID 846601 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 the ester (2.75 g, 0.0106 mole) 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, and the aqueous solution was extracted with ether (20 ml) and adjusted 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 (78%) of the title compound as 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-883d96e6799b4a57ada5dddcba134dae
Source dataset
uspto-grants-1992_08
Patent number
US05137895

Linked notes

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