Toluene → N-[2-(ethylamino)ethyl]-5-nitro-1H-indole-2-carboxamide

HRID 23149

Reaction equation

HRID 23149 reaction equation
C(O[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])C.C1(C)C=CC=CC=1.CCOCC.[CH2:30]([NH:32][CH2:33][CH2:34][NH2:35])[CH3:31]>C(OCC)(=O)C>[CH2:30]([NH:32][CH2:33][CH2:34][NH:35][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])[CH3:31]

Participants

6

Reactant 4

HCID 1140TolueneHCID 3283Diethyl EtherHCID 66071N-EthylethylenediamineHCID 280312Ethyl 5-nitro-1H-indole-2-carboxylate

Product 1

HCID 85801380N-[2-(ethylamino)ethyl]-5-nitro-1H-indole-2-carboxamideYield 82%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A fine powder of 5-nitro-2-indolecarboxylic acid ethyl ester (0.8 g, 3.41 mmol) was suspended in 2 ml of N-ethylethylenediamine under argon and the reaction mixture was stood at 55° C. overnight. The mixture was co-evaporated with toluene to dryness. The brown solid obtained was dissolved in 6 ml of ethyl acetate and 40 ml of ether was added to precipitate the product. After centrifugation, the liquid was poured out and the solid was washed with 30 ml of ether and dried to give small brown crystals (0.77 g, 82%). ESI MS: 277.11 (M+H+), 299.09 (M+Na+). 1H NMR (DMSO-d6) δ8.67 (d, 1H), 8.04 (dd, 1H), 7.55 (d, 1H), 7.37 (s), 3.36 (m, 3H), 2.69 (q, 2H), 2.55 (q, 2H), 0.99 (t, 3H).

Workup

  1. customThe brown solid obtained
  2. customto precipitate the product
  3. additionAfter centrifugation, the liquid was poured out
  4. washthe solid was washed with 30 ml of ether
  5. customdried

Sources & evidence

ORD record
ord-40e663da5a7b4c6aa33aec3ec44db7c1
Source dataset
uspto-grants-2005_02
Patent number
US06849713B2

Linked notes

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