Chlorosuccinimide → 2-Chloro-4-ethyl-6-nitroaniline

HRID 326638

Reaction equation

HRID 326638 reaction equation
[CH2:1]([C:3]1[CH:9]=[CH:8][C:6]([NH2:7])=[C:5]([N+:10]([O-:12])=[O:11])[CH:4]=1)[CH3:2].[Cl:13]N1C(=O)CCC1=O.C(Cl)(Cl)Cl.CCCCCC>CN(C=O)C>[Cl:13][C:8]1[C:6]([NH2:7])=[C:5]([N+:10]([O-:12])=[O:11])[CH:4]=[C:3]([CH2:1][CH3:2])[CH:9]=1

Participants

5

Reactant 3

HCID 31398ChlorosuccinimideHCID 2516744-Ethyl-2-nitroanilineHCID 21585165Chloroform hexane

Product 1

HCID 197351662-Chloro-4-ethyl-6-nitroanilineYield 14.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred solution of 4-ethyl-2-nitroaniline (26.3 g, Example 13a) in DMF (100 ml) at -25° C. was added N-chlorosuccinimide (25.4 g) in portions. The mixture was stirred for 1 h at 0° C. and 30 minutes at ambient temperature before evaporation of the solvent under vacuum. Addition of CHCl3 /hexane (1:1) to the residue followed by filtration removed crystalline succinimide. 6-Chloro-4-ethyl-2-nitroaniline (4.6 g) was isolated from the filtrate after chromatography on silica. δ (360 MHz, CDCl3) 1.22 (3H, t, CH3), 2.56 (2H, q, CH2), 6.38 (2H. s, NH2), 7.4 (1H, d, 5-H) and 7.90 (1H, s, 3-H).

Workup

  1. filtrationfollowed by filtration
  2. customremoved crystalline succinimide

Sources & evidence

ORD record
ord-4651e2520c254b8ebcf0da8f8460d329
Source dataset
uspto-grants-1993_12
Patent number
US05270309

Linked notes

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