[NH2:1][CH:2]([CH2:5][OH:6])[CH2:3][OH:4].[N+]([C:10]1[CH:17]=[CH:16][CH:15]=[C:12]([C:13]#[N:14])[C:11]=1[C:18]#[N:19])([O-])=O.C([O-])([O-])=O.[K+].[K+].C1C=CC=CC=1>CS(C)=O.CC#N>[C:18](#[N:19])[C:11]1[C:12](=[CH:15][CH:16]=[CH:17][CH:10]=1)[C:13]#[N:14].[C:18](#[N:19])[C:11]1[C:12](=[CH:15][CH:16]=[CH:17][CH:10]=1)[C:13]#[N:14].[NH2:1][CH:2]([CH2:5][OH:6])[CH2:3][OH:4]A mixture of serinol (45.8 mg, 0.50 mmol, 1 equiv.), 3-nitrophthalonitrile (258.1 mg, 1.5 mmol, 2.5 equiv.) and K2CO3 (277.4 mg, 2.0 mmol, 4 equiv.) in 3 mL DMSO was stirred at room temperature and monitored periodically by TLC (9:1 benzene:CH3CN). The reaction mixture changed from orange to brown as the reaction occurred. After 90 h, the reaction mixture was heated to 70° C. TLC analysis showed the gradual disappearance of 3-nitrophthalonitrile over the next 8.5 h. The reaction mixture was partitioned between EtOAc and water, and the two layers were separated. The aqueous layer was extracted with EtOAc. This organic extract was combined with the phase-separated organic layer from the original separation, and then this mixture was washed twice with saturated NaHCO3, twice with water, and once with saturated NaCl. TLC analysis of the crude material showed no ninhydrin positive spot. The crude material was purified by flash chromatography using benzene:CH3CN (95:5) to extract the major UV-active spot.
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