[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[CH2:9][CH:8]([NH:13][C:14](=[O:16])[CH3:15])[CH2:7]2)([O-])=O.[C:17](OC(=O)C)(=[O:19])[CH3:18].[H][H]>O1CCCC1.[Ni]>[C:17]([NH:1][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[CH2:9][CH:8]([NH:13][C:14](=[O:16])[CH3:15])[CH2:7]2)(=[O:19])[CH3:18]The mixture of N-(5-nitro-indan-2-yl)-acetamide (20.5 g, 93 mmol) in tetrahydrofuran (200 mL) was combined with acetic anhydride (10 mL) and Raney nickel (5 g) and stirred under an atmosphere of hydrogen gas (in a balloon) at room temperature for 24 h. Additional Raney nickel was added and the balloon recharged with hydrogen gas and stirred an additional 24 h. After removing the Raney nickel by filtration through a celite pad and washing with methanol several times, the filtrate was evaporated to a syrup. The residue was triturated with ether/water and the resulting white solid collected by filtration (9.2 g, 52% yield overall from 2-aminoindan, prepared in Example 20).
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