Sodium Hydroxide → 3-Methoxy-4-o-tolylureidophenylacetic acid

HRID 275891Notes

Reaction equation

HRID 275891 reaction equation
C[O:2][C:3](=[O:24])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12]([NH:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[CH3:21])=[O:13])=[C:7]([O:22][CH3:23])[CH:6]=1.[OH-].[Na+]>CO>[CH3:23][O:22][C:7]1[CH:6]=[C:5]([CH2:4][C:3]([OH:24])=[O:2])[CH:10]=[CH:9][C:8]=1[NH:11][C:12]([NH:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[CH3:21])=[O:13]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 53896144HCID 53896144, compound

Product 1

HCID 114498403-Methoxy-4-o-tolylureidophenylacetic acidYield 84.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A suspension of [3-methoxy-4-(3-o-tolylureido)phenyl]-acetic acid methyl ester (19.43 g, Reference Example 6) in methanol (195 ml) was treated with sodium hydroxide solution (65 ml, 1N) and the mixture was heated at reflux for 1 hour giving a clear solution. The reaction mixture was cooled to room temperature and then filtered. The filtrate was diluted to 390 ml with water, then heated to 50° C. and then acidified to pH 1 by the addition of hydrochloric acid (80 ml, 1N) over 1 hour. The resulting suspension was stirred for a further 30 minutes at 50° C., then allowed to cool to room temperature and then filtered. The solid was washed with twice with water (200 ml) then dried to give the title compound (15.72 g) as a white solid, m. p. 179-181° C. (with decomposition).

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 1 hour
  3. customgiving a clear solution
  4. filtrationfiltered
  5. additionThe filtrate was diluted to 390 ml with water
  6. temperatureheated to 50° C.
  7. additionacidified to pH 1 by the addition of hydrochloric acid (80 ml, 1N) over 1 hour
  8. temperatureto cool to room temperature
  9. filtrationfiltered
  10. washThe solid was washed with twice with water (200 ml)
  11. customthen dried

Sources & evidence

ORD record
ord-56d4a6cf0ac54eb99093cbe77aa69f53
Source dataset
uspto-grants-2002_03
Patent number
US06352977B1

Reaction notes

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