Nitric Acid → HCID 67492871、化合物

反応式

[CH3:1][CH:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]([CH:11]2[CH2:16][CH2:15][N:14]([CH3:17])[CH2:13][CH2:12]2)[C:3]1=[O:18].OS(O)(=O)=O.[N+:24]([O-])([OH:26])=[O:25]>>[CH3:1][CH:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([N+:24]([O-:26])=[O:25])[CH:9]=2)[N:4]([CH:11]2[CH2:16][CH2:15][N:14]([CH3:17])[CH2:13][CH2:12]2)[C:3]1=[O:18]

参加物

反応物 3

HCID 944Nitric Acid

HCID 1118Sulfuric Acid

HCID 67492670HCID 67492670、化合物

生成物 1

HCID 67492871HCID 67492871、化合物収率 61%

実験手順

A solution of 3-methyl-1-(1-methylpiperidin-4-yl)indolin-2-one(0.18 g, 0.736 mmol) in con. H2SO4 (2 mL) was treated with fuming HNO3 (0.034 mL, 0.736 mmol) at −5 to −10° C. (ice+salt) and resulting solution was stirred for 30 min. at this same temperature. The reaction was quenched with addition of crushed ice, and then basified with 1 N NaOH and product was extracted into CH2Cl2 (2×20 mL). The combined CH2Cl2 layer was washed with brine (10 mL) and dried (Na2SO4). The solvent was evaporated and crude was purified by column chromatography (2 M NH3 in MeOH:CH2Cl2, 2.5:97.5) to obtain compound 3-methyl-1-(1-methylpiperidin-4-yl)-5-nitroindolin-2-one (0.13 g, 61%) as a solid. 1H NMR (DMSO-d6) δ: 1.39 (d, 3H, J=7.5 Hz), 1.55-1.62 (m, 2H), 2.01 (t, 2H, J=11.4 Hz), 2.20 (s, 3H), 2.31-2.39 (m, 2H), 2.87 (d, 2H, J=11.4 Hz), 3.63 (q, 1H), 4.06-4.16 (m, 1H), 7.39 (d, 1H, J=9.3 Hz), 8.18-8.22 (m, 2H); ESI-MS (m/z, %) 290 (MH+, 100).