Acetic Anhydride → 1-(2,3-Dihydro-1H-indol-1-yl)ethan-1-one

HRID 2290180Notes

Reaction equation

HRID 2290180 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH2:2]1.[C:10](OC(=O)C)(=[O:12])[CH3:11]>>[C:10]([N:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH2:2]1)(=[O:12])[CH3:11]

Participants

3

Reactant 2

HCID 7918Acetic AnhydrideHCID 10328Indoline

Product 1

HCID 276731-(2,3-Dihydro-1H-indol-1-yl)ethan-1-one

Procedure

To a 3-neck 500 ml round bottom flask containing 108.5 g (0.911 mol) indoline was added acetic anhydride at a rate such as to maintain a temperature below 25° C. After addition (one hour), the reddish sludge was poured into ice water, filtered and washed several times with water. It was allowed to dry overnight and recrystallized from 700 ml of ethanol and gave 116.6 g (72.4% by weight yield) of N-acetylindoline.

Workup

  1. temperatureto maintain a temperature below 25° C
  2. additionAfter addition (one hour)
  3. filtrationfiltered
  4. washwashed several times with water
  5. customto dry overnight
  6. customrecrystallized from 700 ml of ethanol

Sources & evidence

ORD record
ord-4638ba3deb9a4161b7c74f306fe6f680
Source dataset
uspto-grants-1986_10
Patent number
US04615966

Reaction notes

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