Sodium Carbonate → 2-Phenyl-7,8-dihydroquinolin-5(6H)-one

HRID 1872500Notes

Reaction equation

HRID 1872500 reaction equation
NC1CCCC(=O)C=1.[C:9]1([C:15]2[CH:24]=[CH:23][C:22]3[C:21](=[O:25])[CH2:20][CH2:19][CH2:18][C:17]=3[N:16]=2)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.Cl.CN(C)CCC(C1C=CC=CC=1)=O.C(=O)([O-])[O-].[Na+].[Na+]>C(O)(=O)C>[C:9]1([C:15]2[CH:24]=[CH:23][C:22]3[C:21](=[O:25])[CH2:20][CH2:19][CH2:18][C:17]=3[N:16]=2)[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 928441-Propanone, 3-(dimethylamino)-1-phenyl-, hydrochloride (1:1)HCID 186867392-phenyl-7,8-dihydroquinolin-5(6H)-one 3-Aminocyclohexenone

Product 1

HCID 123175922-Phenyl-7,8-dihydroquinolin-5(6H)-oneYield 26.4%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Preparation of 2-phenyl-7,8-dihydroquinolin-5(6H)-one 3-Aminocyclohexenone (5.55 g, 50 mmol) and 3-dimethylaminopropiophenone hydrochloride (10.65 g, 50 mmol) were suspended in glacial acetic acid (15 mL) and heated at reflux for 1 h. The mixture was cooled to room temperature and cautiously poured into 20% aqueous sodium carbonate. After gas evolution ceased the residue was extracted with chloroform, dried over anhydrous sodium carbonate, filtered and evaporated. Purification by chromatography on silica gel using 1:1 chloroform/dichloromethane as eluant provided 2.95 g (26%) of 2-phenyl-7,8-dihydroquinolin-5(6H)-one as an off-white solid, mp 128-130° C.; 1H NMR (CDCl3) δ8.32 (d, 1H), 8.05 (dd, 2H), 7.66 (d, 2H), 7.55-7.42 (m,3H), 3.21 (t, 2H), 2.72 (t, 2H), 2.22 (m, 2H).

Workup

  1. temperatureheated
  2. temperatureat reflux for 1 h
  3. extractionwas extracted with chloroform
  4. dry with materialdried over anhydrous sodium carbonate
  5. filtrationfiltered
  6. customevaporated
  7. customPurification by chromatography on silica gel using 1:1 chloroform/dichloromethane as eluant

Sources & evidence

ORD record
ord-dcb73f237abf4f1c9aa84d23ce0d3415
Source dataset
uspto-grants-2000_08
Patent number
US06110910

Reaction notes

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