Acetic Anhydride → 1-(2-Methyl-2,3-dihydroindol-1-yl)ethanone

HRID 2416962Notes

Reaction equation

HRID 2416962 reaction equation
[CH3:1][CH:2]1[CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[NH:3]1.CN(C1C=CC=CN=1)C.[C:20](OC(=O)C)(=[O:22])[CH3:21]>N1C=CC=CC=1.C(OCC)(=O)C>[C:20]([N:3]1[C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[CH2:10][CH:2]1[CH3:1])(=[O:22])[CH3:21]

Participants

6

Reactant 3

HCID 7918Acetic AnhydrideHCID 218852-DimethylaminopyridineHCID 233052-Methylindoline

Product 1

HCID 43082211-(2-Methyl-2,3-dihydroindol-1-yl)ethanoneYield 100%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of 2-methylindoline (20.0 g, 0.15 mol) and dimethylaminopyridine (500 mg, 5 mmol) in pyridine (50 mL) at room temperature is added acetic anhydride (20 mL). The mixture is stirred at ambient temperature for 18 h, diluted with ethyl acetate, washed with 1 N aqueous hydrochloric acid, water and brine, then dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo to give 26.3 g (100%) of the title compound as an amber oil. MS (ESI+) m/z 176.1 (M+H).

Workup

  1. washwashed with 1 N aqueous hydrochloric acid, water and brine
  2. dry with materialdried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-353f7cd7f2c3486f87111cc136a60ed1
Source dataset
uspto-grants-2004_11
Patent number
US06825225B2

Reaction notes

Loading…