Aluminum(III) Chloride → 1-Acetyl-3,3-dimethylindolin-5-ol

HRID 2360154Notes

Reaction equation

HRID 2360154 reaction equation
C[O:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]([CH2:13][C:14]([CH3:16])=[CH2:15])[C:10](=[O:12])[CH3:11])=[CH:5][CH:4]=1.[Cl-].[Al+3].[Cl-].[Cl-]>ClC1C=CC=CC=1.O.C(OCC)(=O)C>[C:10]([N:9]1[C:6]2[C:5](=[CH:4][C:3]([OH:2])=[CH:8][CH:7]=2)[C:14]([CH3:16])([CH3:15])[CH2:13]1)(=[O:12])[CH3:11]

Participants

6

Reactant 2

HCID 6451240Aluminum(III) ChlorideHCID 86659876N-(4-methoxyphenyl)-N-(2-methylallyl)acetamide

Product 1

HCID 227118171-Acetyl-3,3-dimethylindolin-5-olYield 33.1%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 7964ChlorobenzeneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

A solution of N-(4-methoxyphenyl)-N-(2-methylallyl)acetamide (1.00 g, 4.56 mmol) and aluminium chloride (2.0 g, 15.0 mmol) in 1.0 mL of chlorobenzene was stirred at 110° C. for 3 h. After the reaction mixture was cooled to 0° C., the reaction mixture was diluted with water and ethyl acetate. The separated organic layer was washed with 1 M HCl, saturated NaHCO3 aqueous solution and brine, successively, and dried over MgSO4. After filtration, the filtrate was concentrated in vacuo, and the residue was purified by silica gel column chromatography (hexane/ethyl acetate=70/30 to 20/80) to obtain the title compound (0.31 g, 33%), and followed by recrystallization (hexane/ethyl acetate) to obtain the title compound (0.17 g) as a white solid.

Workup

  1. washThe separated organic layer was washed with 1 M HCl, saturated NaHCO3 aqueous solution and brine
  2. dry with materialsuccessively, and dried over MgSO4
  3. filtrationAfter filtration
  4. concentrationthe filtrate was concentrated in vacuo
  5. customthe residue was purified by silica gel column chromatography (hexane/ethyl acetate=70/30 to 20/80)

Sources & evidence

ORD record
ord-672378ee332d4192a7ee7d978346a5a2
Source dataset
uspto-grants-2014_04
Patent number
US08686024B2

Reaction notes

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