Triethylamine → 1H-Isoindole-1,3(2H)-dione, 2-(6-chloro-4,5-dimethyl-2-pyridinyl)-
Reaction equation
[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:11])[N:3]1[C:12]1[CH:17]=[C:16]([CH3:18])[C:15]([CH3:19])=[CH:14][N+:13]=1[O-].CCN(CC)CC.C([O-])(O)=O.[Na+].O=P(Cl)(Cl)[Cl:35]>>[Cl:35][C:14]1[N:13]=[C:12]([N:3]2[C:2](=[O:1])[C:10]3[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=3)[C:4]2=[O:11])[CH:17]=[C:16]([CH3:18])[C:15]=1[CH3:19]Participants
Procedure
To a solution of 2-(1,3-dioxoisoindolin-2-yl)-4,5-dimethylpyridine 1-oxide (1.5 g, 0.01 mol) in POCl3 (50 mL) was added Et3N (680 mg, 0.01 mol) at room temperature. The mixture was stirred at 80□ for 2 hr, and then carefully poured into the mixture of saturation NaHCO3 solution and ice water. The mixture was extracted with EtOAc (50 mL×3). The combined organic layers were dried over anhydrous Na2SO4, filtered and evaporated under vacuum to give a crude residue that was purified by column chromatography on silica gel (10-15% ethyl acetate in petroleum ether) to give 2-(6-chloro-4,5-dimethylpyridin-2-yl)isoindoline-1,3-dione (650 mg, 41%). 1H NMR (300 MHz, CDCl3) δ 7.97-7.92 (m, 2H), 7.82-7.78 (m, 2H), 7.16 (s, 1H), 2.41 (s, 3H), 2.39 (s, 3H).
Workup
- extractionThe mixture was extracted with EtOAc (50 mL×3)
- dry with materialThe combined organic layers were dried over anhydrous Na2SO4
- filtrationfiltered
- customevaporated under vacuum
- customto give a crude residue that
- customwas purified by column chromatography on silica gel (10-15% ethyl acetate in petroleum ether)
Sources & evidence
- ORD record
- ord-c8badbff8e9b4210be11a6aac012590b
- Source dataset
- uspto-grants-2015_03
- Patent number
- US08969386B2
Reaction notes
Loading…