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

HRID 965543Notes

Reaction equation

HRID 965543 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(N(CC)CC)C.[C:17](OC(=O)C)(=[O:19])[CH3:18].O>C(Cl)(Cl)Cl.CN(C)C1C=CN=CC=1>[C:17]([N:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH2:2]1)(=[O:19])[CH3:18]

Participants

7

Reactant 4

HCID 962WaterHCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 10328Indoline

Product 1

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

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6212ChloroformSolvent3×

Procedure

A solution of 11.9 g of indoline in 100 ml of chloroform is cooled to 0° C. 13.9 ml of triethylamine are added and a solution of 10.4 ml of acetic anhydride in 10 ml of chloroform is then added dropwise, followed by 0.1 g of 4-dimethylaminopyridine. After stirring for two hours at RT, water is added to the reaction mixture, extraction is carried out with chloroform, the organic phase is dried over sodium sulfate and the solvent is evaporated off under vacuum to give 15.44 g of the expected product, which is used as such.

Workup

  1. dry with materialthe organic phase is dried over sodium sulfate
  2. customthe solvent is evaporated off under vacuum

Sources & evidence

ORD record
ord-ba8d9ea7355e4aa08701ef99cb99feda
Source dataset
uspto-grants-1998_06
Patent number
US05773612

Reaction notes

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