반응 #649130

반응 방정식

5-amino-6-nitro-isoindole-1,3-dione

HCl

2-amino-N,N-dimethyl-propylamine

imidazole

Et3N

→

title compound

수율 64.0%

5-Amino-2-(2-dimethylamino-1-methyl-ethyl)-6-nitro-isoindole-1,3-dione

수율 64.0%

용매

dioxane

반응 조건

후처리

1. 1
   기타was sealed in a ChemGlass heavy wall pressure flask
2. 2
   기타the reaction mixture was evaporated to dryness at 95° C. (the bath temperature) under reduced pressure

실험 절차

A mixture of 5-amino-6-nitro-isoindole-1,3-dione (1.66 g, 8.0 mmol), HCl salt of 2-amino-N,N-dimethyl-propylamine (5.3 g, crude, <30 mmol), imidazole (1.36 g, 20 mmol) and Et3N (8.4 mL, 6.07 g, 60 mmol) in dioxane (80 mL) was sealed in a ChemGlass heavy wall pressure flask. After it was heated at 130° C. for 72 h, the reaction mixture was evaporated to dryness at 95° C. (the bath temperature) under reduced pressure. The chromatography of the residue with CH2Cl2/MeOH/28% aqueous NH4OH (240:10:1) afforded the title compound (1.49 g, 64%). 1H NMR (DMSO-d6) δ 1.32 (d, J=6 Hz, 3H, CH3), 2.09 (s, 6H, 2CH3), 2.25 (m, 1H), 2.95 (m, 1H), 4.35 (m, 1H), 7.43 (s, 1H), 8.29 (s, 1H), 8.39 (br s, 2H, NH). ESI-MS m/z 293.1 (MH+).

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