Acetic Anhydride → N-(1H-Indol-5-ylmethyl)acetamide

HRID 1749739Notes

Reaction equation

HRID 1749739 reaction equation
[NH2:1][CH2:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH:7]=[CH:6]2.[C:12](OC(=O)C)(=[O:14])[CH3:13]>>[NH:8]1[C:9]2[C:5](=[CH:4][C:3]([CH2:2][NH:1][C:12](=[O:14])[CH3:13])=[CH:11][CH:10]=2)[CH:6]=[CH:7]1

Participants

3

Reactant 2

HCID 7918Acetic AnhydrideHCID 54791(1H-indol-5-yl)methanamine

Product 1

HCID 22139217N-(1H-Indol-5-ylmethyl)acetamideYield 96%

Procedure

The synthesis was performed with reference to the known literature (International Patent Publication WO2000/75139). 5-Aminomethyl-1H-indole (0.50 g, 3.4 mmol) was added with acetic anhydride (2.0 mL), and the mixture was stirred at room temperature for 3 hours. The mixture was azeotroped twice with toluene under reduced pressure, and the residual solid was washed with ethyl acetate to obtain N-[(1H-indol-5-yl)methyl]acetamide (0.62 g, 96%).

Workup

  1. customThe mixture was azeotroped twice with toluene under reduced pressure
  2. washthe residual solid was washed with ethyl acetate

Sources & evidence

ORD record
ord-fb0ba0cfb4bc4b87be96f1f84ff06edb
Source dataset
uspto-grants-2015_10
Patent number
US09156827B2

Reaction notes

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