Lithium hydroxide, monohydrate → HCID 66759593, compound

HRID 1402844Notes

Reaction equation

HRID 1402844 reaction equation
O.[OH-].[Li+].[Cl:4][C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[CH2:10][N:9]([C:14](=[O:29])[CH:15]([C:22]1[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][CH:23]=1)[CH2:16][C:17]([O:19]CC)=[O:18])[CH2:8]2>O.CO>[Cl:4][C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[CH2:10][N:9]([C:14](=[O:29])[CH:15]([C:22]1[CH:23]=[CH:24][C:25]([Cl:28])=[CH:26][CH:27]=1)[CH2:16][C:17]([OH:19])=[O:18])[CH2:8]2

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 66758946HCID 66758946, compound

Product 1

HCID 66759593HCID 66759593, compoundYield 94.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

With stirring at rt the solution of lithium hydroxide monohydrate (0.29 g) in water (1.5 ml) was added to the solution of ethyl 4-(5-chloro-2-isoindolinyl)-3-(4-chlorophenyl)-4-oxobutanoate (0.64 g) in methanol (10 ml). The cloudy solution was stirred at rt for 2 h. Then the methanol was removed by distillation and the residue was diluted with water (3 ml). With ice-cooling conc. HCl (1 ml) was added dropwise to the stirred solution. The precipitate formed is kept at 0° C. for 0.5 h and collected by suction filtration. After washings with 1M HCl and water the solid is dried in vacuo to provide 4-(5-chloro-2-isoindolinyl)-3-(4-chlorophenyl)-4-oxobutanoic acid (0.56 g) as colourless solid.

Workup

  1. customThen the methanol was removed by distillation
  2. additionthe residue was diluted with water (3 ml)
  3. temperatureWith ice-cooling conc. HCl (1 ml)
  4. additionwas added dropwise to the stirred solution
  5. customThe precipitate formed
  6. waitis kept at 0° C. for 0.5 h
  7. filtrationcollected by suction filtration
  8. washAfter washings with 1M HCl and water the solid
  9. customis dried in vacuo

Sources & evidence

ORD record
ord-42c70d3e01894974aa43def0d9565bf8
Source dataset
uspto-grants-2014_12
Patent number
US08912186B2

Reaction notes

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