CID 223829 → 3-Phenanthrylamine
Reaction equation
C1N(COCCO)[C:4]2NC(N)=[N:13][C:14](=O)[C:3]=2N=1.[CH:17]1[C:30]2C=CC3[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=3)[C:21]=2[CH:20]=[C:19](C(=NO)C)[CH:18]=1>>[CH:25]1[C:24]2[CH:23]=[CH:22][C:21]3[C:30](=[CH:17][CH:18]=[CH:19][CH:20]=3)[C:4]=2[CH:3]=[C:14]([NH2:13])[CH:26]=1Participants
3
Conditions
- Temperature
- 100 °C
Procedure
To 385 g of polyphosphoric acic at 100° C. was added 32 g (0.14 mol) of 1-(3-phenanthryl)ethanone oxime from Step 1 over 30 minutes. The mixture was stirred at 100° C. for 2 hrs, cooled down to room temperature followed by the addition of water/ice. Stirred 30 minutes, filtered and washed with water. This white solid was then placed in 500 mL of methanol and 40 mL of concentrated HCl. The reaction was refluxed overnight, cooled down to room temperature and concentrated down. A mixture of ethyl acetate/water was added to the residue and the resulting solution was made basic with 10 N KOH. The aqueous layer was extracted with ethyl acetate and combined organic layers were washed with water, brine, dried over sodium sulphate and volatiles were removed under reduced pressure to afford 25 g of 3-phenanthrylamine as a beige solid.