Diethylaminoethyl chloride → 1-{4-[2-(Diethylamino)ethoxy]phenyl}-2-phenyl-4(1H)-quinolone

HRID 2072250Notes

Reaction equation

HRID 2072250 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:11](=[O:18])[CH:10]=[C:9]2[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[CH:4][CH:3]=1.C[O-].[Na+].Cl[CH2:29][CH2:30][N:31]([CH2:34][CH3:35])[CH2:32][CH3:33]>C(Cl)(Cl)Cl.ClC1C=CC=CC=1.CO>[CH2:30]([N:31]([CH2:34][CH3:35])[CH2:32][CH2:33][O:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:11](=[O:18])[CH:10]=[C:9]2[C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)=[CH:4][CH:3]=1)[CH3:29]

Participants

7

Reactant 3

HCID 13364Diethylaminoethyl chlorideHCID 10942334Sodium MethoxideHCID 213984761-(4-hydroxyphenyl)-2-phenyl-4(1H)-quinolone

Product 1

HCID 213984861-{4-[2-(Diethylamino)ethoxy]phenyl}-2-phenyl-4(1H)-quinolone

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 6212ChloroformSolventHCID 7964ChlorobenzeneSolvent2×

Procedure

By following a procedure similar to that described in Example 1 and using 49.5 g. 1-(4-hydroxyphenyl)-2-phenyl-4(1H)-quinolone, 10.5 g. sodium methoxide, 500 ml. chlorobenzene, 45 ml. dry methyl alcohol, and 26 g. N-(2-chloroethyl)diethylamine in 80 ml. chlorobenzene there was obtained on evaporation to dryness of the chloroform extract and recrystallization from isopropyl alcohol 32 g. 1-{4-[2-(diethylamino)ethoxy]phenyl}-2-phenyl-4(1H)-quinolone; m.p. 115°-117° C.

Workup

  1. extractionextract
  2. customrecrystallization from isopropyl alcohol 32 g

Sources & evidence

ORD record
ord-fdd29519ef194a8f9ff2486dad0e7c3b
Source dataset
uspto-grants-1977_09
Patent number
US04049715

Reaction notes

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