Aniline → HCID 10823516, Verbindung

Temperatur

90 °C

To stirred polyphosphoric acid (125 g) heated to 90° C. was added 2,3-difluorobenzoic acid (10.00 g, 63.3 mmol) followed by aniline (5.72 g, 61.7 mmol). The reaction mixture was heated at 180°-185° C. for 1 hour (solid dissolved at 135° C.), then the oil bath was removed and distilled water (35 mL) was cautiously added in small portions through the condenser. The oil bath was returned, and the reaction mixture heated at 135°-145° C. for 1 hour. The oil bath was again removed, 3N HCl (55 mL) was added to the solution, the reaction mixture was then poured into water (750 mL) and stirred for one hour. The aqueous solution was filtered through Celite and the filtrate basified with 15% NaOH to a pH of 8. A green solid was collected by filtration and purified by flash column chromatography (methylene chloride). Trituration with hexane yielded the title benzophenone (1.43 g, 10%) as a yellow solid; mp 104°-106° C. 1H--NMR (250 MHz, d6 --DMSO): 6.41 (s, 2H, NH2) 6.60 (d, 2H, J=8.7 Hz, aromatic) 7.22-7.37 (m, 2H, aromatic) 7.50 (d, 2H, J=8.6 Hz, aromatic) 7.53-7.64 (m, 1H, aromatic). MS (CI, CH4): 234 (M+1).

1. temperatureThe reaction mixture was heated at 180°-185° C. for 1 hour
2. dissolution(solid dissolved at 135° C.)
3. customthe oil bath was removed
4. distillationdistilled water (35 mL)
5. additionwas cautiously added in small portions through the condenser
6. temperaturethe reaction mixture heated at 135°-145° C. for 1 hour
7. customThe oil bath was again removed
8. addition3N HCl (55 mL) was added to the solution
9. additionthe reaction mixture was then poured into water (750 mL)
10. filtrationThe aqueous solution was filtered through Celite
11. filtrationA green solid was collected by filtration
12. custompurified by flash column chromatography (methylene chloride)

ORD-Eintrag

ord-c368caedabb84a909696c1605c5b938f

Quelldatensatz

uspto-grants-1993_12

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US05272163