N,N-Dimethylethylenediamine → N-[2-(dimethylamino)ethyl]-6-nitro-1H-indole-2-carboxamide

HRID 23154

Reaction equation

HRID 23154 reaction equation
CO[C:3]([C:5]1[NH:6][C:7]2[C:12]([CH:13]=1)=[CH:11][CH:10]=[C:9]([N+:14]([O-:16])=[O:15])[CH:8]=2)=[O:4].[CH3:17][N:18]([CH3:22])[CH2:19][CH2:20][NH2:21]>>[CH3:17][N:18]([CH3:22])[CH2:19][CH2:20][NH:21][C:3]([C:5]1[NH:6][C:7]2[C:12]([CH:13]=1)=[CH:11][CH:10]=[C:9]([N+:14]([O-:16])=[O:15])[CH:8]=2)=[O:4]

Participants

3

Reactant 2

HCID 66053N,N-DimethylethylenediamineHCID 11816863Methyl 6-nitro-1H-indole-2-carboxylate

Product 1

HCID 85801420N-[2-(dimethylamino)ethyl]-6-nitro-1H-indole-2-carboxamideYield 84%

Procedure

500 mg (2.27 mmole) 6-Nitro-1H-indole-2-carboxylic acid methyl ester was dissolved in 4 mL neat N1,N1-dimethyl-ethane-1,2-diamine, was kept at 55° C. overnight and was evaporated. The oily residue was triturated with n-hexane to give 528 mg (84%) yellow solid which was no further purified. MS: 277.13 (calcd for M+H+:277.13)

Workup

  1. customwas evaporated
  2. customThe oily residue was triturated with n-hexane

Sources & evidence

ORD record
ord-437bfcf42a734cadaba4bc4b65654239
Source dataset
uspto-grants-2005_02
Patent number
US06849713B2

Linked notes

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