2-Bromo-5-nitroaniline → 2-Amino-4-nitrobenzonitrile

HRID 379530Notes

Reaction equation

HRID 379530 reaction equation
Br[C:2]1[CH:8]=[CH:7][C:6]([N+:9]([O-:11])=[O:10])=[CH:5][C:3]=1[NH2:4].[Cu][C:13]#[N:14]>CN(C)C=O.N1C=CC=CC=1>[C:13]([C:2]1[CH:8]=[CH:7][C:6]([N+:9]([O-:11])=[O:10])=[CH:5][C:3]=1[NH2:4])#[N:14]

Participants

5

Reactant 2

HCID 826072-Bromo-5-nitroanilineHCID 178418546HCID 178418546, compound

Product 1

HCID 111478972-Amino-4-nitrobenzonitrileYield 70.4%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
160 °C

Procedure

To a solution of 2-bromo-5-nitroaniline (5.0 g, 23 mmol) in dimethylforamide (100 ml) and pyridine (20ml) was stirred with copper(I) cyanide (2.05 g, 64 mmol). The mixture was then heated to 160° C. for 48 hrs. The reaction was then cooled to room temperature and filtered through celite, the celite was washed with ethyl acetate. The solvent was evaporated and chromatography of the resulting solid on silica gel (25%EtOAc/Hexane) gave the desired product (2.64 g, 70%). 1H NMR (CD3COCD3): δ7.75 (s, 1H), 7.70 (d, 1H), 7.44 (dd, 1H), 6.25(bs, 2H).

Workup

  1. temperatureThe reaction was then cooled to room temperature
  2. filtrationfiltered through celite
  3. washthe celite was washed with ethyl acetate
  4. customThe solvent was evaporated

Sources & evidence

ORD record
ord-9e0dd6b53b3c450aaf5afeef1f29566a
Source dataset
uspto-grants-2001_10
Patent number
US06300325B1

Reaction notes

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