6-Nitro-m-toluidine → N-(2-ethoxycarbonylethyl)-5-methyl-2-nitroaniline
Reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([N+:9]([O-:11])=[O:10])=[C:6]([CH:8]=1)[NH2:7].Br[CH:13]([CH3:19])[C:14]([O:16][CH2:17][CH3:18])=[O:15].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH2:17]([O:16][C:14]([CH2:13][CH2:19][NH:7][C:6]1[CH:8]=[C:2]([CH3:1])[CH:3]=[CH:4][C:5]=1[N+:9]([O-:11])=[O:10])=[O:15])[CH3:18]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 150 °C
Procedure
A mixture of 5-methyl-2-nitroaniline (3.00 g), ethyl bromopropionate (5.35 g) and potassium carbonate (8.18 g) in N,N-dimethylformamide (20 ml) was stirred at 150° C. for 4 hours and the suspension was cooled to ambient temperature. After being filtered, the filtrate was diluted with ethyl acetate and the solution was washed successively with saturated sodium bicarbonate aqueous solution and brine. Drying over magnesium sulfate, filtering and the removal of solvents afforded a crude product. The crude product was triturated with diethyl ether-n-hexane (1:1) to give N-(2-ethoxycarbonylethyl)-5-methyl-2-nitroaniline (2.83 g) as a yellow prisms.
Workup
- temperaturethe suspension was cooled to ambient temperature
- filtrationAfter being filtered
- additionthe filtrate was diluted with ethyl acetate
- washthe solution was washed successively with saturated sodium bicarbonate aqueous solution and brine
- dry with materialDrying over magnesium sulfate
- filtrationfiltering
- customthe removal of solvents
- customafforded a crude product
- customThe crude product was triturated with diethyl ether-n-hexane (1:1)
Sources & evidence
- ORD record
- ord-65cf8ec9703e4909a77a4d82230c864b
- Source dataset
- uspto-grants-1996_05
- Patent number
- US05521170
Reaction notes
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