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

HRID 2254610Notes

Reaction equation

HRID 2254610 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 mmoles) 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 resultant precipitate was filtered, washed with water, air dried, and recrystallized from ethyl acetate to yield 2.03 g (78%) 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. filtrationA resultant precipitate was filtered
  5. washwashed with water, air
  6. customdried
  7. customrecrystallized from ethyl acetate

Sources & evidence

ORD record
ord-02a4994f0c0241dc84fc7c631bbbac03
Source dataset
uspto-grants-1993_08
Patent number
US05236931

Reaction notes

Loading…