Acetic Anhydride → N-[2-(5-nitro-1H-indol-3-yl)ethyl]acetamide

HRID 1581715Notes

Reaction equation

HRID 1581715 reaction equation
[N+:1]([C:4]1[CH:15]=[C:14]2[C:7]([NH:8][CH:9]=[C:10]2[CH2:11][CH2:12][NH2:13])=[CH:6][CH:5]=1)([O-:3])=[O:2].[C:16](OC(=O)C)(=[O:18])[CH3:17]>N1C=CC=CC=1>[N+:1]([C:4]1[CH:15]=[C:14]2[C:7](=[CH:6][CH:5]=1)[NH:8][CH:9]=[C:10]2[CH2:11][CH2:12][NH:13][C:16](=[O:18])[CH3:17])([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 1512951H-Indole-3-ethanamine, 5-nitro-

Product 1

HCID 906605N-[2-(5-nitro-1H-indol-3-yl)ethyl]acetamide

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

5-Nitrotryptamine (6 mmol) is dissolved in pyridine (15 ml) and treated with acetic anhydride (7 mmol) 20 min at 27° C. The solvents are removed in vacuo, the residue taken into a small amount of methanol and passed through a short plug of silica with 5% methanol-chloroform eluent. Product-containing fractions are pooled, evaporated and dried thoroughly at <0.1 mm Hg.

Workup

  1. customThe solvents are removed in vacuo
  2. customevaporated
  3. customdried thoroughly at <0.1 mm Hg

Sources & evidence

ORD record
ord-db4856665db84ee1b25db3f39ad9b717
Source dataset
uspto-grants-2004_05
Patent number
US06730707B2

Reaction notes

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