Acetic Acid → 4-Acetoxy-1-tosyl-1,2-dihydroquinoline

HRID 726699Notes

Reaction equation

HRID 726699 reaction equation
[NH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:11])[CH2:3][CH2:2]1.[C:12]1([CH3:22])[CH:17]=[CH:16][C:15]([S:18]([OH:21])(=[O:20])=O)=[CH:14][CH:13]=1.C(=O)(O)[O-].[Na+].[C:28](O)(=[O:30])[CH3:29]>>[C:28]([O:11][C:4]1[C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[N:1]([S:18]([C:15]2[CH:14]=[CH:13][C:12]([CH3:22])=[CH:17][CH:16]=2)(=[O:20])=[O:21])[CH2:2][CH:3]=1)(=[O:30])[CH3:29]

Participants

5

Reactant 4

HCID 176Acetic AcidHCID 6101p-Toluenesulfonic acidHCID 1171582,3-dihydroquinolin-4(1H)-oneHCID 516892Sodium Bicarbonate

Product 1

HCID 197068564-Acetoxy-1-tosyl-1,2-dihydroquinoline

Procedure

1,2,3,4-Tetrahydroquinolin-4-one (2.00 g) and 114 mg of p-toluenesulfonic acid were dissolved in 30 ml of acetic acid isopropenyl ether, and the solution was heated under reflux for 2 days simultaneously evaporating acetic acid. Then, saturated sodium bicarbonate aqueous solution was added and the mixture was extracted with ethyl acetate, followed by drying on anhydrous magnesium sulfate. After evaporating the solvent, the resulting residue was crystallized from chloroform-diethyl ether-hexane to obtain 518 mg of 4-acetoxy-1-tosyl-1,2-dihydroquinoline.

Workup

  1. temperaturethe solution was heated
  2. extractionthe mixture was extracted with ethyl acetate
  3. dry with materialby drying on anhydrous magnesium sulfate
  4. customAfter evaporating the solvent
  5. customthe resulting residue was crystallized from chloroform-diethyl ether-hexane

Sources & evidence

ORD record
ord-b8582ee352a644bdb77fb50f2b066a37
Source dataset
uspto-grants-1998_01
Patent number
US05710150

Reaction notes

Loading…