HCID 53929406, compound → 2-Phenylquinolin-8-amine

HRID 2359387Notes

Reaction equation

HRID 2359387 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][CH:7]=[C:8]2[C:13]=1[N:12]=[C:11]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[CH:10]=[CH:9]2)([O-:3])=[O:2]>CO.[Pd]>[N+:1]([C:4]1[CH:5]=[CH:6][CH:7]=[C:8]2[C:13]=1[N:12]=[C:11]([C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)[CH:10]=[CH:9]2)([O-:3])=[O:2].[C:14]1([C:11]2[CH:10]=[CH:9][C:8]3[C:13](=[C:4]([NH2:1])[CH:5]=[CH:6][CH:7]=3)[N:12]=2)[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

5

Reactant 1

HCID 53929406HCID 53929406, compound

Product 2

HCID 199558612-Phenylquinolin-8-amineYield 169.3%HCID 53929406HCID 53929406, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

8-Nitro-2-phenylquinoline was prepared according to the procedure outlined by Elderfield et al in J. American Chemical Society (1946), vol 68, p. 1589. In a typical run, 8-nitro-2-phenylquinoline (510 mg) was dissolved in 100 mL of MeOH. After the addition of 10% Pd on C (50 mg), the reaction mixture was thoroughly purged with nitrogen. It was then stirred vigorously at room temperature under 1 atm of hydrogen for 18 h. The reaction mixture was filtered through Celite and the filtrate was concentrated under reduced pressure to afford 380 mg of 2-phenylquinolin-8-amine. MS (ESI) calcd for C15H12N2 (m/z): 220.10. found: 221 [M+1].

Workup

  1. customthe reaction mixture was thoroughly purged with nitrogen
  2. filtrationThe reaction mixture was filtered through Celite
  3. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-c3391f33be7f4a39bd979410db8642b7
Source dataset
uspto-grants-2014_04
Patent number
US08685970B2

Reaction notes

Loading…