Ethyl Acetate → 5-Cyclopropyl-2-(5-fluoro-2-nitro-phenylamino)-benzonitrile

HRID 131333Notes

Reaction equation

HRID 131333 reaction equation
[NH2:1][C:2]1[CH:9]=[CH:8][C:7]([CH:10]2[CH2:12][CH2:11]2)=[CH:6][C:3]=1[C:4]#[N:5].F[C:14]1[CH:19]=[C:18]([F:20])[CH:17]=[CH:16][C:15]=1[N+:21]([O-:23])=[O:22].O.[OH-].[Li+].C(OCC)(=O)C>CS(C)=O>[CH:10]1([C:7]2[CH:8]=[CH:9][C:2]([NH:1][C:14]3[CH:19]=[C:18]([F:20])[CH:17]=[CH:16][C:15]=3[N+:21]([O-:23])=[O:22])=[C:3]([CH:6]=2)[C:4]#[N:5])[CH2:11][CH2:12]1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 679672,4-DifluoronitrobenzeneHCID 168937Lithium hydroxide, monohydrateHCID 451221932-Amino-5-cyclopropylbenzonitrile

Product 1

HCID 586258745-Cyclopropyl-2-(5-fluoro-2-nitro-phenylamino)-benzonitrileYield 25%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Heat a solution of 2-amino-5-cyclopropyl-benzonitrile (0.980 g, 6.16 mmol) with 2,4-difluoro-1-nitro-benzene (0.676 g, 6.16 mmol) and lithium hydroxide monohydrate (0.517 g, 12.33 mmol) in DMSO (12 ml) to 55° C. for 18 hours. Cool the reaction to ambient temperature and then add approximately 150 ml of ice water and stir the mixture for one hour. Precipitate the title compound and collect by filtration. Purify the solid via flash chromatography eluting with a linear gradient starting with 100% hexanes and going to 70% hexanes: 30% ethyl acetate to obtain 0.452 g (1.52 mmol, 25% yield) of the title compound as a yellow amorphous solid: Mass Spectrum (m/e): 298 (M+1).

Workup

  1. temperatureCool
  2. customthe reaction to ambient temperature
  3. customPrecipitate the title compound
  4. filtrationcollect by filtration
  5. customPurify the solid via flash chromatography
  6. washeluting with a linear gradient

Sources & evidence

ORD record
ord-ce15a0812ce44dff94aa943eae17c226
Source dataset
uspto-grants-2008_06
Patent number
US07384934B2

Reaction notes

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