Ethanol → ethyl 1-ethyl-5-nitro-1H-indole-2-carboxylate

HRID 489987Notes

Reaction equation

[CH2:1]([O:3][C:4]([C:6]1[NH:7][C:8]2[C:13]([CH:14]=1)=[CH:12][C:11]([N+:15]([O-:17])=[O:16])=[CH:10][CH:9]=2)=[O:5])[CH3:2].[H-].[Na+].[CH2:20](I)[CH3:21].C(O)C>CN(C=O)C.O>[CH2:1]([O:3][C:4]([C:6]1[N:7]([CH2:20][CH3:21])[C:8]2[C:13]([CH:14]=1)=[CH:12][C:11]([N+:15]([O-:17])=[O:16])=[CH:10][CH:9]=2)=[O:5])[CH3:2]

Participants

Conditions

Temperature: 0 °C

Procedure

5-Nitro-1H-indole-2-carboxylic acid ethyl ester (5 g, 21.3 mol) was dissolved in DMF (50 mL). The reaction mixture was cooled to 0° C. Sodium hydride (1.02, 25.5 mmol, 60% in mineral oil) was added to the above solution in portions over 10 minutes. The mixture was stirred at room temperature for 30 minutes. Ethyl iodide (6.5 g, 42 mmol) was added to the above solution and the reaction mixture was stirred overnight. Ethanol (30 mL) was added to the reaction mixture and the mixture was poured into cold water (800 mL). The crude product was collected by filtration and used directly in next step without further purification (5 g).

Workup

stirringthe reaction mixture was stirred overnight
filtrationThe crude product was collected by filtration
customused directly in next step without further purification (5 g)

Sources & evidence

ORD record: ord-13501dd3bd5b4f519d0a30a10976668d
Source dataset: uspto-grants-2005_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06979692B2

Reaction notes

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