Acetic Acid → N,N-Diethyl-2-(4-methylphenyl)-4-quinolinecarboxamide

HRID 986270Notes

Reaction equation

HRID 986270 reaction equation
C([Li])CCC.[CH2:6]([NH:8][CH2:9][CH3:10])[CH3:7].[CH3:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]2[CH:27]=[C:26]([C:28]([O:30]CC)=O)[C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[N:19]=2)=[CH:14][CH:13]=1.C(O)(=O)C>CCCCCC.O1CCCC1.O>[CH2:6]([N:8]([CH2:9][CH3:10])[C:28]([C:26]1[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[N:19]=[C:18]([C:15]2[CH:16]=[CH:17][C:12]([CH3:11])=[CH:13][CH:14]=2)[CH:27]=1)=[O:30])[CH3:7]

Participants

8

Reactant 4

HCID 176Acetic AcidHCID 8021DiethylamineHCID 20158366HCID 20158366, compoundHCID 178418339Butyllithium

Product 1

HCID 1358956N,N-Diethyl-2-(4-methylphenyl)-4-quinolinecarboxamide

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Conditions

Temperature
0 °C

Procedure

A 1.6M solution of butyllithium in hexane (22.5 ml) is added, at ambient temperature and under a nitrogen atmosphere, to diethylamine (5.5 ml) in anhydrous tetrahydrofuran (50 ml). After stirring for 15 minutes, the mixture is cooled to 0° C. and ethyl 2-(4-methylphenyl)-quinoline-4-carboxylate (5.25 g) is then introduced slowly. The mixture is stirred for 2 hours at ambient temperature. Acetic acid is then added slowly, at ambient temperature and with stirring, until decolouration takes place and a yellow solution is obtained. Water (100 ml) is then added, the tetrahydrofuran is evaporated off under reduced pressure and the residue is extracted with ethyl acetate (3×100 ml). The organic phase is washed with water, dried over magnesium sulphate and evaporated under reduced pressure. The residue is chromatographed on silica gel with a cyclohexane/ethyl acetate mixture (80/20) as the eluant. After recrystallisation from isopropyl ether of the crude product isolated in this way, N,N-diethyl-2-(4-methylphenyl)-quinoline-4-carboxamide (1.1 g), melting at 145° C., is obtained.

Workup

  1. stirringThe mixture is stirred for 2 hours at ambient temperature
  2. stirringwith stirring, until decolouration
  3. customa yellow solution is obtained
  4. customthe tetrahydrofuran is evaporated off under reduced pressure
  5. extractionthe residue is extracted with ethyl acetate (3×100 ml)
  6. washThe organic phase is washed with water
  7. dry with materialdried over magnesium sulphate
  8. customevaporated under reduced pressure
  9. customThe residue is chromatographed on silica gel with a cyclohexane/ethyl acetate mixture (80/20) as the eluant
  10. customAfter recrystallisation from isopropyl ether of the crude product

Sources & evidence

ORD record
ord-6455f8e9f5db48129eb13395ff738f65
Source dataset
uspto-grants-1987_12
Patent number
US04711890

Reaction notes

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