Triethylamine → HCID 9885691, compound

HRID 1683901Notes

Reaction equation

HRID 1683901 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[C:5]2[CH2:11][CH2:12][N:13]([CH3:15])[CH3:14].Cl[C:17]1[C:22]([N+:23]([O-:25])=[O:24])=[CH:21][C:20]([N+:26]([O-:28])=[O:27])=[CH:19][N:18]=1.C(N(CC)CC)C>O1CCCC1>[CH3:15][N:13]([CH3:14])[CH2:12][CH2:11][C:5]1[C:4]2[C:8](=[CH:9][CH:10]=[C:2]([NH:1][C:17]3[C:22]([N+:23]([O-:25])=[O:24])=[CH:21][C:20]([N+:26]([O-:28])=[O:27])=[CH:19][N:18]=3)[CH:3]=2)[NH:7][CH:6]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 757382-Chloro-3,5-dinitropyridineHCID 118202113-(2-DIMETHYLAMINO-ETHYL)-1H-INDOL-5-YLAMINE

Product 1

HCID 9885691HCID 9885691, compoundYield 7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

5-Amino-3-(2-dimethylaminoethyl)indole and 2-chloro-3,5-dinitropyridine were used. Triethylamine was used as base, tetrahydrofuran was used as solvent, and the reaction was stirred at room temperature for 1 hour. Direct filtration of the reaction mixture afforded a red solid which was recrystallized in ethanol to afford the title compound (7%) as a red solid: mp, 194.0°-195.0° C.; 13C NMR (DMSO-d6) δ152.2, 150.7, 134.7, 134.1, 131.2, 128.2, 127.1, 126.7, 123.9, 119.1, 114.8, 112.7, 111.4, 59.7, 44.9, 22.8; HRMS calculated for C17H18N6O4 370.1391, found 370.1358. Anal. calcd. for C17H18N6O4.1/2H2O: C, 53.82; H, 5.04; N, 22.15. Found: C, 53.55; H, 4.58; N, 21.98.

Workup

  1. filtrationDirect filtration of the reaction mixture
  2. customafforded a red solid which
  3. customwas recrystallized in ethanol

Sources & evidence

ORD record
ord-321e511fbfa245a896dd99f050184b39
Source dataset
uspto-grants-1997_06
Patent number
US05639752

Reaction notes

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