Aniline → 4'-[(2-Ethylquinolin-4-yloxy)methyl]biphenyl-2-carbonitrile

HRID 1757288Notes

Reaction equation

HRID 1757288 reaction equation
C(C1CC(=O)C2C(=CC=CC=2)N=1)C.C1(C(C2NN=NN=2)(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.NC1C=CC=CC=1.C(CC(OC)=O)(=O)CC.[CH2:54]([C:57]1[CH:66]=[C:65]([O:67][CH2:68][C:69]2[CH:74]=[CH:73][C:72]([C:75]3[CH:80]=[CH:79][CH:78]=[CH:77][C:76]=3[C:81]3N=NN(C(C4C=CC=CC=4)(C4C=CC=CC=4)C4C=CC=CC=4)[N:85]=3)=[CH:71][CH:70]=2)[C:64]2[C:59](=[CH:60][CH:61]=[CH:62][CH:63]=2)[N:58]=1)[CH2:55]C.C(=O)([O-])[O-].[K+].[K+]>CN1CCCC1=O.O>[CH2:54]([C:57]1[CH:66]=[C:65]([O:67][CH2:68][C:69]2[CH:74]=[CH:73][C:72]([C:75]3[C:76]([C:81]#[N:85])=[CH:77][CH:78]=[CH:79][CH:80]=3)=[CH:71][CH:70]=2)[C:64]2[C:59](=[CH:60][CH:61]=[CH:62][CH:63]=2)[N:58]=1)[CH3:55]

Participants

9

Reactant 6

HCID 6115AnilineHCID 11430Potassium CarbonateHCID 121699Methyl 3-oxovalerateHCID 150208512-ethyl-3H-quinolin-4-oneHCID 151144952-propyl-4-[(2'-(2-triphenylmethyl-2H-tetrazol-5-yl)biphenyl-4-yl)methoxy]quinolineHCID 178420198HCID 178420198, compound

Product 1

HCID 150208494'-[(2-Ethylquinolin-4-yloxy)methyl]biphenyl-2-carbonitrileYield 111.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A mixture of 2-ethyl-4-quinolone (1.73 g), (prepared by a similar method to that described in Org. Syn., Coll. Vol. III, p.374 and p.593 from aniline and methyl propionylacetate), 4'-bromomethylbiphenyl-2-carbonitrile (A) (3.1 g) and solid potassium carbonate (1.81 g) in N-methylpyrrolidone (40 ml) were stirred for 36 hours under nitrogen. The mixture was then added dropwise to water (100 ml) at 15°-25° C. and stirred for 30 minutes. The suspended solid was collected by filtration, washed with water, and dried at 60° C. under vacuum. The solid was recrystallised from tert-butyl methyl ether to give 4'-[(2-ethylquinolin-4-yloxy)methyl]-biphenyl-2-carbonitrile as a solid (1.9 g), m.p. 151°-153° C.; NMR(CDCl3): 1.4(t, 3H), 2.97(q,2H), 5.35(s,2H), 6.76(s,1H), 7.4-7.6(m, 3H), 7.6-7.8(m, 6H), 8.0(d, 1H), 8.25(d, 1H).

Workup

  1. custom(prepared by a similar method to
  2. filtrationThe suspended solid was collected by filtration
  3. washwashed with water
  4. customdried at 60° C. under vacuum
  5. customThe solid was recrystallised from tert-butyl methyl ether

Sources & evidence

ORD record
ord-8203257a05404fa9b0e833f839e0b4b4
Source dataset
uspto-grants-1995_08
Patent number
US05444071

Reaction notes

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