Sodium hydride → N-(4,5-dimethoxy-2-nitrophenyl)-N',N'-dimethylethylenediamine

HRID 373064Notes

Reaction equation

[CH3:1][O:2][C:3]1[C:9]([O:10][CH3:11])=[CH:8][C:6]([NH2:7])=[C:5]([N+:12]([O-:14])=[O:13])[CH:4]=1.Cl.Cl[CH2:17][CH2:18][N:19]([CH3:21])[CH3:20].[H-].[Na+]>CN(C)C=O.[OH-].[Na+]>[CH3:1][O:2][C:3]1[C:9]([O:10][CH3:11])=[CH:8][C:6]([NH:7][CH2:17][CH2:18][N:19]([CH3:21])[CH3:20])=[C:5]([N+:12]([O-:14])=[O:13])[CH:4]=1

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of 4,5-dimethoxy-2-nitroaniline (0.81 g) and 2-chloroethyldimethylamine hydrochloride (0.73 g) in N,N-dimethylformamide (20 ml) was added sodium hydride (0.36 g) in small portions with ice-cooling and the reaction mixture was heated at 60° C. for 2 hours. The reaction mixture was diluted with 1N aqueous sodium hydroxide solution and extracted with ethyl acetate. The organic layer was successively washed with water and saturated aqueous sodium chloride solution and dried over anhydrous sodium sulfate. The solvent was then distilled off under reduced pressure and the residue was purified by silica gel chromatography (eluent:chloroform:methanol=15:1) to give 0.77 g of N-(4,5-dimethoxy-2-nitrophenyl)-N',N'-dimethylethylenediamine.

Workup

temperaturecooling
extractionextracted with ethyl acetate
washThe organic layer was successively washed with water and saturated aqueous sodium chloride solution
dry with materialdried over anhydrous sodium sulfate
distillationThe solvent was then distilled off under reduced pressure
customthe residue was purified by silica gel chromatography (eluent:chloroform:methanol=15:1)

Sources & evidence

ORD record: ord-347687bd589543e98b1cb60f2ce4f893
Source dataset: uspto-grants-1992_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05162318

Reaction notes

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