Tetrahydrofuran → 4-(2-Chlorophenyl)-3-(4-hydroxycinnamoylamino)-6,8-dimethylquinoline

HRID 259867

Reaction equation

HRID 259867 reaction equation
[NH2:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([C:11]=1[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[Cl:18])=[CH:9][C:8]([CH3:19])=[CH:7][C:6]=2[CH3:20].C([O:24][C:25]1[CH:35]=[CH:34][C:28]([CH:29]=[CH:30][C:31](Cl)=[O:32])=[CH:27][CH:26]=1)(=O)C.O1CCCC1.C(=O)([O-])O.[Na+]>O>[Cl:18][C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=1[C:11]1[C:10]2[C:5](=[C:6]([CH3:20])[CH:7]=[C:8]([CH3:19])[CH:9]=2)[N:4]=[CH:3][C:2]=1[NH:1][C:31](=[O:32])[CH:30]=[CH:29][C:28]1[CH:34]=[CH:35][C:25]([OH:24])=[CH:26][CH:27]=1

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 516892Sodium BicarbonateHCID 5903202-Propenoyl chloride, 3-[4-(acetyloxy)phenyl]-, (E)-HCID 104465363-Amino-4-(2-chlorophenyl)-6,8-dimethylquinoline

Product 1

HCID 537838394-(2-Chlorophenyl)-3-(4-hydroxycinnamoylamino)-6,8-dimethylquinolineYield 78.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 3-amino-4-(2-chlorophenyl)-6,8-dimethylquinoline (282 mg), 4-acetoxycinnamoyl chloride (250 mg) and tetrahydrofuran (5 ml) was stirred at room temperature for 6 hours. After being diluted with water and made neutral with a sodium hydrogen carbonate saturated solution, the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with water and dried (MgSO4). The solvent was removed, and the residue was dissolved in tetrahydrofuran-methanol solution (1:1, 6 ml). Then, 2N-hydrochloric acid was added to the solution which was thereafter stirred at room temperature for 1.5 hours. The resultant solution was diluted with water, adjusted to pH 4 by addition of 2N-hydrochloric acid and extracted with ethyl acetate. The ethyl acetate layer was washed with water and dried (MgSO4). The resultant was removed to give crystals of 4-(2-chlorophenyl)-3-(4-hydroxycinnamoylamino)-6,8-dimethylquinoline (335 mg, 78.3%). The obtained crystals were recrystallized from ethanol to afford colorless needles.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe ethyl acetate layer was washed with water
  3. dry with materialdried (MgSO4)
  4. customThe solvent was removed
  5. dissolutionthe residue was dissolved in tetrahydrofuran-methanol solution (1:1, 6 ml)
  6. additionThen, 2N-hydrochloric acid was added to the solution which
  7. stirringwas thereafter stirred at room temperature for 1.5 hours
  8. additionThe resultant solution was diluted with water
  9. additionadjusted to pH 4 by addition of 2N-hydrochloric acid
  10. extractionextracted with ethyl acetate
  11. washThe ethyl acetate layer was washed with water
  12. dry with materialdried (MgSO4)
  13. customThe resultant was removed

Sources & evidence

ORD record
ord-a6f47f76823144b09bba314b9cb8fa83
Source dataset
uspto-grants-1996_06
Patent number
US05523407

Linked notes

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