Water → 1-Acetyl-3-(2-carboxyethyl)-4,6-dimethylindoline

HRID 1107958Notes

Reaction equation

HRID 1107958 reaction equation
[C:1]([N:4]1[C:12]2[C:7](=[C:8]([CH3:14])[CH:9]=[C:10]([CH3:13])[CH:11]=2)[CH:6]([CH2:15][CH2:16][C:17]#N)[CH2:5]1)(=[O:3])[CH3:2].[OH-:19].[K+].[OH2:21]>CCO>[C:1]([N:4]1[C:12]2[C:7](=[C:8]([CH3:14])[CH:9]=[C:10]([CH3:13])[CH:11]=2)[CH:6]([CH2:15][CH2:16][C:17]([OH:21])=[O:19])[CH2:5]1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 962WaterHCID 14797Potassium HydroxideHCID 222473041-Acetyl-3-(2-cyanoethyl)-4,6-dimethylindoline

Product 1

HCID 222473451-Acetyl-3-(2-carboxyethyl)-4,6-dimethylindoline

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1-Acetyl-3-(2-cyanoethyl)-4,6-dimethylindoline (4.5 g) was dissolved in EtOH (150 ml), and a solution of KOH (10.4 g) in water (50 ml) was added, which was followed by refluxing for 15 hr. EtOH was evaporated under reduced pressure, and the aqueous layer was adjusted to weak acidic with 6N hydrochloric acid and extracted with CHCl3 (100 ml). The CHCl3 layer was washed with water and dried over anhydrous sodium sulfate. CHCl3 was evaporated under reduced pressure. The residue was dissolved in CHCl3 (20 ml) and Ac2O (1.9 g) was added, which was followed by stirring at room temperature for 1 hr. CHCl3 (100 ml) was added, and the mixture was washed with water and dried over anhydrous sodium sulfate. CHCl3 was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: CHCl3 /MeOH=50/1-10/1) to give 3.4 g of 1-acetyl-3-(2-carboxyethyl)-4,6-dimethylindoline.

Workup

  1. temperatureby refluxing for 15 hr
  2. customEtOH was evaporated under reduced pressure
  3. extractionextracted with CHCl3 (100 ml)
  4. washThe CHCl3 layer was washed with water
  5. dry with materialdried over anhydrous sodium sulfate
  6. customCHCl3 was evaporated under reduced pressure
  7. dissolutionThe residue was dissolved in CHCl3 (20 ml)
  8. additionAc2O (1.9 g) was added
  9. additionCHCl3 (100 ml) was added
  10. washthe mixture was washed with water
  11. dry with materialdried over anhydrous sodium sulfate
  12. customCHCl3 was evaporated under reduced pressure
  13. customThe residue was purified by silica gel column chromatography (eluent: CHCl3 /MeOH=50/1-10/1)

Sources & evidence

ORD record
ord-4fedcb92ca144c1b8248486b48a8512f
Source dataset
uspto-grants-2000_05
Patent number
US06063806

Reaction notes

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