Ethyl Acetate → 2-(4-Fluoro-2-nitro-phenylamino)-5-methyl-benzonitrile

HRID 131320

Reaction equation

HRID 131320 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH2:8])=[C:4]([N+:9]([O-:11])=[O:10])[CH:3]=1.F[C:13]1[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][C:14]=1[C:15]#[N:16].O.[OH-].[Li+].C(OCC)(=O)C>CS(C)=O.ClCCl>[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:13]2[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][C:14]=2[C:15]#[N:16])=[C:4]([N+:9]([O-:11])=[O:10])[CH:3]=1

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 677694-Fluoro-2-nitroanilineHCID 168937Lithium hydroxide, monohydrateHCID 27745842-Fluoro-5-methylbenzonitrile

Product 1

HCID 210934602-(4-Fluoro-2-nitro-phenylamino)-5-methyl-benzonitrileYield 45.2%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
55 °C

Procedure

Combine 4-fluoro-2-nitro-phenylamine (2.9 g, 18.50 mmol), 2-fluoro-5-methyl-benzonitrile (2.5 g, 18.50 mmol) and lithium hydroxide monohydrate (2.4 g, 57.20 mmol) in methyl sulfoxide (DMSO, 40 ml). Heat the resulting mixture to 55° C. for 40 hours. Cool the reaction mixture to ambient temperature, then pour into approximately 250 ml of ice water and stir for one hour. Filter the resulting mixture and collect the precipitate. Chromatograph the solid using flash chromatography and elute with mobile phase: 90% hexanes, 5% ethyl acetate, and 5% dichloromethane to obtain 2.267 g of the title compound (8.36 mmol, 45% yield) as an orange amorphous solid: Mass Spectrum (m/e): 272(M+1).

Workup

  1. temperatureCool the reaction mixture to ambient temperature
  2. filtrationFilter the resulting mixture
  3. customcollect the precipitate
  4. washelute with mobile phase

Sources & evidence

ORD record
ord-b3b2628025d8478b9fcf42782ca39456
Source dataset
uspto-grants-2008_06
Patent number
US07384934B2

Linked notes

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