Nitric Acid → HCID 10379608, 화합물

반응식

[C:1]([NH:4][C:5]1[C:6]([Cl:15])=[CH:7][C:8]([Cl:14])=[C:9]([CH:13]=1)[C:10]([OH:12])=[O:11])(=[O:3])[CH3:2].OS(O)(=O)=O.[N+:21]([O-])([OH:23])=[O:22]>>[C:1]([NH:4][C:5]1[C:13]([N+:21]([O-:23])=[O:22])=[C:9]([C:8]([Cl:14])=[CH:7][C:6]=1[Cl:15])[C:10]([OH:12])=[O:11])(=[O:3])[CH3:2]

참가 물질

반응물 3

HCID 944Nitric Acid3회

HCID 1118Sulfuric Acid3회

HCID 2833165-(Acetylamino)-2,4-dichlorobenzoic acid

생성물 1

HCID 10379608HCID 10379608, 화합물수율 81%

실험 절차

5-Acetamido-2,4-dichlorobenzoic acid 1-4 (40.0 g, 0.161 mol) was added in portions to a cooled mixture of concentrated H2SO4 (400 mL) and concentrated nitric acid (400 mL) at 5° C. After stirring for 2 h concentrated H2SO4 (100 mL)/concentrated nitric acid (100 mL) was added. After another 90 min concentrated H2SO4 (400 mL)/concentrated nitric acid (200 mL) was added and stirring was continued for a further 2 h. The reaction mixture was cautiously poured onto ice resulting in the formation of a yellow precipitate. The product was collected by filtration then extracted into EtOAc. The combined organic layers were washed with H2O, brine, dried over Na2SO4, filtered and concentrated to provide the nitro compound 1-5 as a yellow/orange solid (38.1 g, 81% yield). 1H NMR (400 MHz, d6-DMSO) δ1.99 (s, 3H), 8.21 (s, 1H), 10.27 (s, 1H).