F[C:2]1[CH:9]=[CH:8][C:7]([CH3:10])=[CH:6][C:3]=1[C:4]#[N:5].[Cl:11][C:12]1[CH:17]=[CH:16][C:15]([NH2:18])=[C:14]([N+:19]([O-:21])=[O:20])[CH:13]=1.O.[OH-].[Li+].O>CS(C)=O.C(OCC)(=O)C>[Cl:11][C:12]1[CH:17]=[CH:16][C:15]([NH:18][C:2]2[CH:9]=[CH:8][C:7]([CH3:10])=[CH:6][C:3]=2[C:4]#[N:5])=[C:14]([N+:19]([O-:21])=[O:20])[CH:13]=1
Heat a solution of 2-fluoro-5-methyl-benzonitrile (2.0 g, 14.80 mmol) with 4-chloro-2-nitro-phenylamine (2.5 g, 14.80 mmol) and lithium hydroxide monohydrate (1.24 g, 29.60 mmol) in DMSO (30 ml) to 55° C. for 14 hours. Add an additional 0.61 g (14.80 mmol) of lithium hydroxide monohydrate, and increase heating to 70° C., continue for another 14 hours. Cool the reaction to ambient temperature and pour into a mixture of 100 ml water and 200 ml ethyl acetate. Extract with three 200 ml portions of ethyl acetate. Combine organic layers, dry over sodium sulfate and evaporate solvent. Purify the residue via flash chromatography eluting with a step gradient starting with 90% hexanes: 10% ethyl acetate and going to 40% hexanes: 60% ethyl acetate to obtain 1.63 g (5.67 mmol, 38% yield) of the title compound as a red-orange amorphous solid: Mass Spectrum (m/e): 288 (M+1).
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