Ethanol hydrochloride → 1-Acetyl-3-(2-ethoxycarbonylethyl)-4,6-dimethylindoline

HRID 1107959Notes

Reaction equation

HRID 1107959 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]([OH:19])=[O:18])[CH2:5]1)(=[O:3])[CH3:2].Cl.[CH3:21][CH2:22]O>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]([O:19][CH2:21][CH3:22])=[O:18])[CH2:5]1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 21887872Ethanol hydrochlorideHCID 222473451-Acetyl-3-(2-carboxyethyl)-4,6-dimethylindoline

Product 1

HCID 222473291-Acetyl-3-(2-ethoxycarbonylethyl)-4,6-dimethylindoline

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1-Acetyl-3-(2-carboxyethyl)-4,6-dimethylindoline (3.4 g) was dissolved in EtOH (50 ml) and 10N HCl-EtOH (3.9 ml) was added, which was followed by refluxing for 30 min. EtOH was evaporated under reduced pressure and AcOEt (100 ml) was added. After washing with water, the mixture was dried over anhydrous sodium sulfate. AcOEt was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: CHCl3 /MeOH=50/1-10/1) to give 3.3 g of 1-acetyl-3-(2-ethoxycarbonylethyl)-4,6-dimethylindoline.

Workup

  1. temperatureby refluxing for 30 min
  2. customEtOH was evaporated under reduced pressure and AcOEt (100 ml)
  3. additionwas added
  4. washAfter washing with water
  5. dry with materialthe mixture was dried over anhydrous sodium sulfate
  6. customAcOEt was evaporated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (eluent: CHCl3 /MeOH=50/1-10/1)

Sources & evidence

ORD record
ord-fc747cbd39a14944a7ad197886069ec6
Source dataset
uspto-grants-2000_05
Patent number
US06063806

Reaction notes

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