N.C(O)C.[Br:5][C:6]1[C:14]2[O:15][CH2:16][CH2:17][C:13]=2[C:12]2/[C:11](=[CH:18]/[C:19]#[N:20])/[CH2:10][CH2:9][C:8]=2[CH:7]=1.[H][H]>[Ni].C(O)C>[BrH:5].[CH2:17]1[CH2:16][O:15][C:14]2[CH:6]=[CH:7][C:8]3[CH2:9][CH2:10][CH:11]([CH2:18][CH2:19][NH2:20])[C:12]=3[C:13]1=2
Raney nickel (0.4 g, W2) and 4 M ammonia/ethanol solution (10 ml) were added to an ethanol (30 ml) suspension of (E)-(4-bromo-1,6,7,8-tetrahydro-2H-indeno[5,4-b]furan-8-ylidene)acetonitrile (0.44 g, 1.59 mmols) and stirred in a hydrogen atmosphere (at from 4 to 5 atmospheres) at room temperature for 5 hours. The reaction mixture was filtered, and the filtrate was concentrated under reduced pressure. The residue was dissolved in ethanol (50 ml), and 5% palladium-carbon (1 g, containing 50% water) was added thereto and stirred in a hydrogen atmosphere (at ordinary pressure) at room temperature for 4 hours. The reaction mixture was filtered, and the filtrate was concentrated under reduced pressure to obtain 0.42 g (yield: 93%) of the target compound. This was amorphous.
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