Water → HCID 13520521, compound

HRID 1380579Notes

Reaction equation

HRID 1380579 reaction equation
[CH2:1]([C:3]1[C:7]([C:8]2[NH:9][C:10]3[C:15]([C:16]=2[C:17](=[O:24])[CH2:18][CH2:19][C:20]([O:22]C)=[O:21])=[CH:14][CH:13]=[CH:12][CH:11]=3)=[C:6]([CH3:25])[O:5][N:4]=1)[CH3:2].[OH-].[Na+].CCOCC.O>CO>[CH2:1]([C:3]1[C:7]([C:8]2[NH:9][C:10]3[C:15]([C:16]=2[C:17](=[O:24])[CH2:18][CH2:19][C:20]([OH:22])=[O:21])=[CH:14][CH:13]=[CH:12][CH:11]=3)=[C:6]([CH3:25])[O:5][N:4]=1)[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 3283Diethyl EtherHCID 14798Sodium HydroxideHCID 86740257HCID 86740257, compound

Product 1

HCID 13520521HCID 13520521, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of the above 2-(3-ethyl-5-methyl-4-isoxazolyl)-γ-oxo-indole-3-butanoic acid, methyl ester in 250 ml methanol is treated with 250 ml of 2N sodium hydroxide solution; and the mixture is heated 15 minutes to 40°-45° and then stirred at room temperature for 1 hour. Ether and water are added to the mixture and the layers then separated. The ether layer is washed with water; after which the combined aqueous layers are washed with ether, treated with charcoal and filtered through celite. The aqueous basic solution is made acidic by careful addition of concentrated HCl and extracted with ether. The ether solution is then washed with water, brine, dried over MgSO4, filtered and evaporated. The resulting foam is crystallized to give the title compound, m.p. 98°-110° C.

Workup

  1. temperatureand the mixture is heated 15 minutes to 40°-45°
  2. customthe layers then separated
  3. washThe ether layer is washed with water
  4. washafter which the combined aqueous layers are washed with ether
  5. additiontreated with charcoal
  6. filtrationfiltered through celite
  7. additionThe aqueous basic solution is made acidic by careful addition of concentrated HCl
  8. extractionextracted with ether
  9. washThe ether solution is then washed with water, brine
  10. dry with materialdried over MgSO4
  11. filtrationfiltered
  12. customevaporated
  13. customThe resulting foam is crystallized

Sources & evidence

ORD record
ord-91a9e5893ca54d089788beb0b37d87a3
Source dataset
uspto-grants-1986_04
Patent number
US04582848

Reaction notes

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