[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=O.[NH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCl.O>[C:11]1([NH:10][CH2:5][C:4]2[CH:3]=[C:2]([OH:1])[CH:9]=[CH:8][CH:7]=2)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1To a solution of 3-hydroxybenzaldehyde (1.05 g, 8.6 mmol) and aniline (821 μL, 9.0 mmol) in dichloromethane (35 mL) was added acetic acid (516 μL, 9.0 mmol). The reaction mixture was stirred at room temperature for 24 hours. Sodium triacetoxyborohydride (4.55 g, 21.5 mmol) was added, and the reaction was stirred at room temperature for 24 hours. Water was added to quench the reaction and the mixture was diluted with dichloromethane. The organic layer was washed with brine, passed through a hydrophobic frit and the solvent was removed in vacuo to afford the title compound as a brown oil (1.7 g, quantitative yield).
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