1: 85 percent / Na2CO3, KI / dimethylformamide / 16 h / Ambient temperature 2: 2.78 g / NH2NH2*H2O / Raney Ni / tetrahydrofuran 3: 43 percent View Scheme

1: 85 percent / Na2CO3, KI / dimethylformamide / 16 h / Ambient temperature 2: 2.78 g / NH2NH2*H2O / Raney Ni / tetrahydrofuran 3: 43 percent View Scheme

1: 1) oxalyl chloride, 2) K2CO3 / 1) toluene, DMF, 55 deg C, 30 min, 2) H2O, toluene, 95 min, 0 deg C 2: 67 percent / BH3*SMe2 / tetrahydrofuran / 16 h / Heating 3: 62 percent / K2CO3 / dimethylformamide / 24 h / Ambient temperature 4: H2 / 10percent Pd/C / methanol / 1.58 h 5: methanol / 24 h View Scheme

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in methanol 24 h; Yield given;