[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[C:4]([CH2:9][CH2:10][C:11]2[CH:16]=[CH:15][C:14]([CH2:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[CH:13][CH:12]=2)[C:3]=1[N+:22]([O-])=O>C(O)C.[Pd]>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[C:4]([CH2:9][CH2:10][C:11]2[CH:12]=[CH:13][C:14]([CH2:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[CH:15][CH:16]=2)[C:3]=1[NH2:22]10% Pd/C (600 mg) was added under nitrogen to a stirred solution of the product from step (c) (10.9 g) in ethanol (150 ml) and the mixture hydrogenated at room temperature at a pressure of 1 atm. H2 for 3.5 hours (uptake 2300 ml). The mixture was filtered, the residue washed with ethanol, and the filtrate evaporated under reduced pressure to give an oil which crystallised on standing to give 8.0 g of the desired product.
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