Benzoic Acid → HCID 10608703, compound

Temperature

220 °C

To stirred 90° C. polyphosphoric acid (150 g) was added 18.32 g (15.0 mmol) of benzoic acid and 8.33 g (7.5 mmol) of 3-fluoroaniline and the bath temperature raised to 220° C. and held there for 1 hour. A solution was obtained at about 130° C. The heating bath was removed and the stirred mixture (sublimate above the solution) was treated cautiously with 60 mL of water. The mixture was stirred at 140°-155° C. for 1 hour, the heating bath removed, 50 mL of 3N HCl added, the mixture poured into 750 mL of water and filtered through a pad of Celite. The filtrate was basified with 15% sodium hydroxide and the resulting solid collected. The 1.88 g of solid was chromatographed on silica gel (methylene chloride) to yield 1.15 g (7%) of white fluffy 4-amino-2-fluorobenzophenone, mp 133-5° C. 1H NMR (250 MHz, CDCl3): 4.20 (s, 2H, NH2) 6.33-6.50 (m, 2H, aromatic) 7.27-7.55 (m, 4H, aromatic) 7.76-7.79 (m, 2H, aromatic). MS (CI, CH4) 216 (M+1). Analysis for C13H10FNO: Calculated: C, 72.55; H, 4.68; N, 6.51 Found: C, 72.20; H, 4.64; N, 6.45

1. customA solution was obtained at about 130° C
2. customThe heating bath was removed
3. additionthe stirred mixture (sublimate above the solution) was treated cautiously with 60 mL of water
4. customthe heating bath removed
5. addition50 mL of 3N HCl added
6. additionthe mixture poured into 750 mL of water
7. filtrationfiltered through a pad of Celite
8. customthe resulting solid collected
9. customThe 1.88 g of solid was chromatographed on silica gel (methylene chloride)

ORD record

ord-0685eb44230c455b8d6735d313c36ff6

Source dataset

uspto-grants-1995_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05474999