1-Chloro-2,4-Dinitrobenzene → HCID 19040750, compound

HRID 1683906Notes

Reaction equation

HRID 1683906 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[CH:22]=[CH:21][C:20]([N+:23]([O-:25])=[O:24])=[CH:19][C:18]=1[N+:26]([O-:28])=[O:27].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:21]3[CH:22]=[CH:17][C:18]([N+:26]([O-:28])=[O:27])=[CH:19][C:20]=3[N+:23]([O-:25])=[O:24])[CH:3]=2)[NH:7][CH:6]=1

Participants

5

Reactant 3

HCID 61-Chloro-2,4-DinitrobenzeneHCID 8471TriethylamineHCID 118202113-(2-DIMETHYLAMINO-ETHYL)-1H-INDOL-5-YLAMINE

Product 1

HCID 19040750HCID 19040750, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

5-Amino-3-(2-dimethylaminoethyl)indole and 1-chloro-2,4-dinitrobenzene were used. Triethylamine was used as base, tetrahydrofuran was used as solvent, and the reaction was stirred at room temperature for 2 hours. Chromatography afforded the title compound (73%) as a dark red solid: mp, 177.0°-179.0° C.; 13C NMR (DMSO-d6) δ148.2, 135.6, 135.2, 130.1, 129.6, 128.2, 127.9, 124.3, 123.5, 119.6, 116.9. 116.3, 113.3, 112.5, 60.0, 45.2, 23.0; FAB HRMS calculated for C18H19N5O4.[H+ ]370.1517, found 370.1492.

Sources & evidence

ORD record
ord-58e01cbe53f84c02bec08db1d9f556ce
Source dataset
uspto-grants-1997_06
Patent number
US05639752

Reaction notes

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