CID 223829 → 3-Phenanthrylamine

HRID 2117975Notes

Reaction equation

HRID 2117975 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]=1

Participants

3

Reactant 2

HCID 223829CID 223829HCID 178508935HCID 178508935, compound

Product 1

HCID 746913-PhenanthrylamineYield 92.4%

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.

Workup

  1. temperaturecooled down to room temperature
  2. stirringStirred 30 minutes
  3. filtrationfiltered
  4. washwashed with water
  5. temperatureThe reaction was refluxed overnight
  6. temperaturecooled down to room temperature
  7. concentrationconcentrated down
  8. additionA mixture of ethyl acetate/water
  9. additionwas added to the residue
  10. extractionThe aqueous layer was extracted with ethyl acetate
  11. washwere washed with water, brine
  12. dry with materialdried over sodium sulphate and volatiles
  13. customwere removed under reduced pressure

Sources & evidence

ORD record
ord-f7b5fa2c5ff34eb0b62b00f1bb48b709
Source dataset
uspto-grants-2008_10
Patent number
US07442716B2

Reaction notes

Loading…