Sodium Hydroxide → 1-Ethoxycarbonyl-5-chloro-3-phenylisoindole-2-acetic acid

HRID 1679059Notes

Reaction equation

HRID 1679059 reaction equation
C([O:3][C:4](=[O:27])[CH2:5][N:6]1[C:14]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[C:13]2[C:8]([CH:9]=[CH:10][C:11]([Cl:21])=[CH:12]2)=[C:7]1[C:22]([O:24][CH2:25][CH3:26])=[O:23])C.[OH-].[Na+]>C(O)C>[CH2:25]([O:24][C:22]([C:7]1[N:6]([CH2:5][C:4]([OH:27])=[O:3])[C:14]([C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)=[C:13]2[C:8]=1[CH:9]=[CH:10][C:11]([Cl:21])=[CH:12]2)=[O:23])[CH3:26]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 545612521-Ethoxycarbonyl-5-chloro-3-phenylisoindole-2-acetic acid ethyl ester

Product 1

HCID 203518001-Ethoxycarbonyl-5-chloro-3-phenylisoindole-2-acetic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A suspension of 19.5 g. of 1-ethoxycarbonyl-5-chloro-3-phenylisoindole-2-acetic acid ethyl ester in 150 ml. of ethanol is treated with 60 ml. of 1.0-N sodium hydroxide and boiled at reflux for 30 minutes. After allowing the mixture to stand for 2 hours in an ice-bath, the crystallized sodium salt is removed by filtration under vacuum, washed with ethanol and then dissolved in a mixture of 400 ml. of ethanol and 250 ml. of water. The obtained solution is acidified with 160 ml. of 0.5-N hydrochloric acid with stirring at 40°-45° C. and then left to stand in an ice-bath for 2 hours. The separated acid is removed by filtration under vacuum, washed with water and then dissolved in 750 ml. of methylene chloride. The aqueous layer is separated, the organic phase dried over sodium sulfate and concentrated to about 200 ml. Then, the crystallized colorless acid is removed by filtration under suction and washed with a small amount of methylene chloride, and there is obtained 1-ethoxycarbonyl-5-chloro-3-phenylisoindole-2-acetic acid; melting point 217°-220° C. (decomposition).

Workup

  1. additionA suspension of 19.5 g
  2. temperatureat reflux for 30 minutes
  3. customthe crystallized sodium salt is removed by filtration under vacuum
  4. washwashed with ethanol
  5. dissolutiondissolved in a mixture of 400 ml
  6. waitleft
  7. waitto stand in an ice-bath for 2 hours
  8. customThe separated acid is removed by filtration under vacuum
  9. washwashed with water
  10. dissolutiondissolved in 750 ml
  11. customThe aqueous layer is separated
  12. dry with materialthe organic phase dried over sodium sulfate
  13. concentrationconcentrated to about 200 ml
  14. customThen, the crystallized colorless acid is removed by filtration under suction
  15. washwashed with a small amount of methylene chloride

Sources & evidence

ORD record
ord-427679a9657f45d1a8db23b0e5fd8bd7
Source dataset
uspto-grants-1978_03
Patent number
US04077978

Reaction notes

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