Dibutylamine → 3-Chloro-7-(dibutylamino)quinoline-8-carbonitrile

HRID 1980750Notes

Reaction equation

HRID 1980750 reaction equation
[Cl:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[C:7](Cl)[C:6]=2[C:13]#[N:14].[CH2:15]([NH:19][CH2:20][CH2:21][CH2:22][CH3:23])[CH2:16][CH2:17][CH3:18]>COC(O)CC>[Cl:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[C:7]([N:19]([CH2:20][CH2:21][CH2:22][CH3:23])[CH2:15][CH2:16][CH2:17][CH3:18])[C:6]=2[C:13]#[N:14]

Participants

4

Reactant 2

HCID 8148DibutylamineHCID 130907923,7-Dichloroquinoline-8-carbonitrile

Product 1

HCID 132065253-Chloro-7-(dibutylamino)quinoline-8-carbonitrileYield 82.5%

Reagents, catalysts & solvents 1

HCID 3032390Propylene glycol methyl etherSolvent

Procedure

22.3 g of 3,7-dichloro-8-cyanoquinoline and 26 g of di-n-butylamine in 300 ml of methoxypropanol were refluxed for 12 hours, the solution was cooled, and the precipitated solid was filtered off under suction and recrystallized from a mixture of naphtha and toluene. 26 g of 3-chloro-8-cyano-7-di-n-butylaminoquinoline of melting point 112° C. were obtained. Yield: 82.5% of theory.

Workup

  1. temperaturethe solution was cooled
  2. filtrationthe precipitated solid was filtered off under suction
  3. customrecrystallized from a mixture of naphtha and toluene

Sources & evidence

ORD record
ord-c37acfd092e046d1b6355f31453914ac
Source dataset
uspto-grants-1985_04
Patent number
US04511393

Reaction notes

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