Acetic Anhydride → 1-Acetyl-1H-indol-3-yl acetate

HRID 1162165Notes

Reaction equation

HRID 1162165 reaction equation
[C:1]([O:4][C:5](=O)[CH3:6])(=[O:3])[CH3:2].C(N(CC)CC)C.[C:15]([N:18]([CH2:28]C(O)=O)[C:19]1C=[CH:26][CH:25]=[CH:24][C:20]=1C(O)=O)(=[O:17])[CH3:16]>O>[C:15]([N:18]1[C:19]2[C:6](=[CH:26][CH:25]=[CH:24][CH:20]=2)[C:5]([O:4][C:1](=[O:3])[CH3:2])=[CH:28]1)(=[O:17])[CH3:16]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 7151462-[Acetyl(carboxymethyl)amino]benzoic acid

Product 1

HCID 5836021-Acetyl-1H-indol-3-yl acetateYield 86.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a stirred mixture of acetic anhydride (46.29 g, 0.45 mol) and triethylamine (13.77 g, 0.14 mol), 2-(N-acetylcarboxymethylamino)benzoic acid of Example 1b (11.36 g, 0.048 mol) was added at room temperature. The mixture was refluxed for 20 min and concentrated in vacuum to give an oily residue. Water (350 mL) was added under vigorous stirring, and the mixture was refrigerated overnight. The solid product was collected, washed with water and air-dried to give 9.0 g (86%) of the product which was used in the next step without purification.

Workup

  1. additionwas added at room temperature
  2. temperatureThe mixture was refluxed for 20 min
  3. concentrationconcentrated in vacuum
  4. customto give an oily residue
  5. customThe solid product was collected
  6. washwashed with water
  7. customair-dried

Sources & evidence

ORD record
ord-be5e60906ebe4785b1746ab10e2ebf17
Source dataset
uspto-grants-2010_10
Patent number
US07820691B2

Reaction notes

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