Benzoic Acid → HCID 10608703, compound
Reaction equation
[C:1]([OH:9])(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F:10][C:11]1[CH:12]=[C:13]([CH:15]=[CH:16][CH:17]=1)[NH2:14]>>[NH2:14][C:13]1[CH:15]=[CH:16][C:17]([C:1]([C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[O:9])=[C:11]([F:10])[CH:12]=1Participants
Conditions
- Temperature
- 220 °C
Procedure
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).
Workup
- customA solution was obtained at about 130° C
- customThe heating bath was removed
- additionthe stirred mixture (sublimate above the solution) was treated cautiously with 60 mL of water
- customthe heating bath removed
- addition50 mL of 3N HCl added
- additionthe mixture poured into 750 mL of water
- filtrationfiltered through a pad of Celite
- customthe resulting solid collected
- customThe 1.88 g of solid was chromatographed on silica gel (methylene chloride)
Sources & evidence
- ORD record
- ord-bc629939edf447e89153385b048d94da
- Source dataset
- uspto-grants-1993_12
- Patent number
- US05272163
Reaction notes
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