Sulfuric Acid → 4-Fluoro-2-methoxy-5-nitroaniline

반응식

[F:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[C:4]([O:9][CH3:10])[CH:3]=1.OS(O)(=O)=O.[N+:16]([O-])([O-:18])=[O:17].[K+].[NH4+].[OH-]>>[F:1][C:2]1[C:8]([N+:16]([O-:18])=[O:17])=[CH:7][C:5]([NH2:6])=[C:4]([O:9][CH3:10])[CH:3]=1

참가 물질

반응물 4

HCID 1118Sulfuric Acid

HCID 14923Ammonium Hydroxide

HCID 24434Potassium Nitrate

HCID 135322284-Fluoro-2-methoxyaniline

생성물 1

HCID 574290724-Fluoro-2-methoxy-5-nitroaniline수율 77.4%

실험 절차

4-Fluoro-2-methoxyaniline (2.4 g, 17.00 mmol) was added portionwise to concentrated H2SO4 (15 mL) which was cooled in a ice/water bath, and where the temperature was kept below 15° C. during the addition. The mixture was stirred until all the solid that formed had dissolved. KNO3 (0.815 mL, 17.00 mmol) was added portionwise such that the temperature was maintained below 10° C. The mixture was stirred overnight and then poured onto ice/water. The mixture was basified with concentrated NH4OH. The resulting solid was filtered off and then dissolved in CH2Cl2, washed with water, dried (Na2SO4) and concentrated onto silica. Purification by FCC, eluting with 50-0% heptane in CH2Cl2 gave the title compound (2.450 g, 77%) as a yellow crystalline solid; 1H NMR: 3.91 (3H, s), 5.21 (2H, s), 7.03 (1H, d), 7.35 (1H, d); m/z: ES+ MH+ 187.4.