Lithium Hydroxide → 2-(5-Fluoro-2-nitro-phenylamino)-5-isopropyl-benzonitrile

HRID 131330Notes

Reaction equation

HRID 131330 reaction equation
[NH2:1][C:2]1[CH:9]=[CH:8][C:7]([CH:10]([CH3:12])[CH3:11])=[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].[OH-].[Li+].C(OCC)(=O)C>CS(C)=O>[F:20][C:18]1[CH:17]=[CH:16][C:15]([N+:21]([O-:23])=[O:22])=[C:14]([NH:1][C:2]2[CH:9]=[CH:8][C:7]([CH:10]([CH3:12])[CH3:11])=[CH:6][C:3]=2[C:4]#[N:5])[CH:19]=1

Participants

6

Reactant 4

HCID 3939Lithium HydroxideHCID 8857Ethyl AcetateHCID 679672,4-DifluoronitrobenzeneHCID 210934632-Amino-5-isopropylbenzonitrile

Product 1

HCID 586259572-(5-Fluoro-2-nitro-phenylamino)-5-isopropyl-benzonitrileYield 16.4%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Heat a solution of 2-amino-5-isopropyl-benzonitrile (1.21 g, 7.55 mmol) with 2,4-difluoro-1-nitro-benzene (1.20 g, 7.55 mmol) and lithium hydroxide (0.54 g, 22.66 mmol) in DMSO (15 ml) to 70° C. for 18 hours. Cool the reaction to ambient temperature and then pour into approximately 200 ml of ice water and stir for one hour. The title compound precipitates and is colleted by filtration. Purify the solid via flash chromatography eluting with a 95% hexanes: 5% ethyl acetate mobile phase to obtain 0.372 g (1.24 mmol, 16% yield) of the title compound as an orange amorphous solid: Mass Spectrum (m/e): 298 (M−1).

Workup

  1. temperatureCool
  2. customthe reaction to ambient temperature
  3. customThe title compound precipitates
  4. filtrationis colleted by filtration
  5. customPurify the solid via flash chromatography
  6. washeluting with a 95% hexanes

Sources & evidence

ORD record
ord-c4491ebbc188498abc9e2e87309ba20e
Source dataset
uspto-grants-2008_06
Patent number
US07384934B2

Reaction notes

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