Methanol → N-(2'-carboxyphenyl)-5,6,7,8-tetrahydro-9-oxo-xanthene-2-carboxylic acid amide

HRID 1577995Notes

Reaction equation

HRID 1577995 reaction equation
CO.C[O:4][C:5]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[NH:13][C:14]([C:16]1[CH:29]=[CH:28][C:27]2[O:26][C:25]3[CH2:24][CH2:23][CH2:22][CH2:21][C:20]=3[C:19](=[O:30])[C:18]=2[CH:17]=1)=[O:15])=[O:6].[OH-].[Na+]>O>[C:5]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[NH:13][C:14]([C:16]1[CH:29]=[CH:28][C:27]2[O:26][C:25]3[CH2:24][CH2:23][CH2:22][CH2:21][C:20]=3[C:19](=[O:30])[C:18]=2[CH:17]=1)=[O:15])([OH:6])=[O:4]

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 12952241N-(2'-methoxycarbonylphenyl)-5,6,7,8tetrahydro-9-oxo-xanthene-2-carboxylic acid amide

Product 1

HCID 12952244N-(2'-carboxyphenyl)-5,6,7,8-tetrahydro-9-oxo-xanthene-2-carboxylic acid amideYield 71.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 80 ml of a methanol suspension containing 4.31 of N-(2'-methoxycarbonylphenyl)-5,6,7,8tetrahydro-9-oxo-xanthene-2-carboxylic acid amide obtained in Example 43 was added 10 ml of an aqueous solution containing 0.48 g of sodium hydroxide. The mixture was heated for 3 hours under refluxing and stirring conditions. The solvent was then removed by distillation to give a residue which was dissolved in hot water and filtered. The filtrate was acidified with concentrated hydrochloric acid to separate a yellowish white deposit. The deposit was collected by filtration, washed with water and then air-dried. Finally, the deposit was recrystallized from acetic acid to obtain 2.96 g (yield: 71.8%) of N-(2'-carboxyphenyl)-5,6,7,8-tetrahydro-9-oxo-xanthene-2-carboxylic acid amide.

Workup

  1. temperatureThe mixture was heated for 3 hours
  2. temperatureunder refluxing
  3. customThe solvent was then removed by distillation
  4. customto give a residue which
  5. filtrationfiltered
  6. customto separate a yellowish white deposit
  7. filtrationThe deposit was collected by filtration
  8. washwashed with water
  9. customair-dried
  10. customFinally, the deposit was recrystallized from acetic acid

Sources & evidence

ORD record
ord-5ff5c8e107954dabbc86de5688df063d
Source dataset
uspto-grants-1981_09
Patent number
US04290954

Reaction notes

Loading…