Acetic Anhydride → HCID 25000400, compound

HRID 2381276Notes

Reaction equation

HRID 2381276 reaction equation
[NH2:1][CH2:2][CH2:3][C:4]1[C:12]([O:13][CH3:14])=[CH:11][C:10]([O:15][CH3:16])=[C:9]2[C:5]=1[CH:6]=[CH:7][NH:8]2.[C:17](OC(=O)C)(=[O:19])[CH3:18]>>[C:17]([NH:1][CH2:2][CH2:3][C:4]1[C:12]([O:13][CH3:14])=[CH:11][C:10]([O:15][CH3:16])=[C:9]2[C:5]=1[CH:6]=[CH:7][NH:8]2)(=[O:19])[CH3:18]

Participants

3

Reactant 2

HCID 7918Acetic AnhydrideHCID 68554298HCID 68554298, compound

Product 1

HCID 25000400HCID 25000400, compoundYield 54%

Procedure

To a cold solution of 4-(2′-aminoethyl)-5,7-dimethoxyindole (0.29 g, 1.3 mmol) in the (10 cm3) were added TEA (0.9 cm3) and acetic anhydride (0.5 cm3). The ice bath was removed and the solution stirred for 15 hours using the method of Spadoni et al. The solvent was evaporated under vacuum, and the residue was taken up into ethyl acetate and washed with a saturated aqueous solution of NaHC03, followed by saturated NaCl solution. The organic layer was dried with MgS04 and concentrated to give a crude solid, which was chromatographed on silica, using ethyl acetate:methanol (95:5), to give 4-[2′-(N-acetyl)aminoethyl]-5,7-dimethoxyindole (0.19 g, 54%) as a brown viscous oil.

Workup

  1. customThe ice bath was removed
  2. customwas evaporated under vacuum
  3. washwashed with a saturated aqueous solution of NaHC03
  4. customThe organic layer was dried with MgS04
  5. concentrationconcentrated
  6. customto give a crude solid, which
  7. customwas chromatographed on silica

Sources & evidence

ORD record
ord-9b2504c55fd64d5eb8e45c03c18c1b26
Source dataset
uspto-grants-2012_09
Patent number
US08258173B2

Reaction notes

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