Triethylamine → HCID 21474177, compound

HRID 2294167Notes

Reaction equation

HRID 2294167 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[CH:5]2.Cl[C:12]1[C:17]([N+:18]([O-:20])=[O:19])=[CH:16][CH:15]=[CH:14][N:13]=1.C(N(CC)CC)C>C(O)C>[N+:18]([C:17]1[C:12]([NH:1][C:2]2[CH:3]=[C:4]3[C:8](=[CH:9][CH:10]=2)[NH:7][CH:6]=[CH:5]3)=[N:13][CH:14]=[CH:15][CH:16]=1)([O-:20])=[O:19]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 788675-AminoindoleHCID 796132-Chloro-3-nitropyridine

Product 1

HCID 21474177HCID 21474177, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

5-Aminoindole (0.264 g, 2.00 mmoles) and 2-chloro-3-nitropyridine (0.476 g, 3.00 mmoles) were combined with triethylamine (0.42 ml, 3.01 mmoles) in absolute ethanol. The reaction was heated at room temperature under nitrogen for 72 hours. The resulting reaction mixture was filtered to afford the title compound (69%) as a dark red solid. Mp, 162.0°-163.5° C.; Rf =0.6 in diethyl ether; 13C NMR (DMSO-d6) δ155.6, 150.5, 135.5, 133.5, 129.7, 127.9, 127.6, 125.9, 118.5, 115.0, 113.4, 111.2, 101.2. Analytical calculated for C13H10N4O2 : C, 61.41; H, 3.96; N, 22.04. Found: 61.22; H, 3.80; N, 22.08.

Workup

  1. customThe resulting reaction mixture
  2. filtrationwas filtered

Sources & evidence

ORD record
ord-0cff519598744b84a384421d4e1878cb
Source dataset
uspto-grants-1997_11
Patent number
US05688809

Reaction notes

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