Ethylene Glycol → HCID 18317309, compound

HRID 1700704Notes

Reaction equation

HRID 1700704 reaction equation
[Cl:1][C:2]1[CH:6]=[CH:5][S:4][C:3]=1[CH:7]1[CH2:16][C:15]2[N:14]=[CH:13][CH:12]=[C:11]([CH3:17])[C:10]=2[C:9](=[O:18])[CH2:8]1.[CH2:19](O)[CH2:20][OH:21].C1(C)C=CC(S(O)(=O)=O)=CC=1.C(=O)([O-])O.[Na+]>C1(C)C=CC=CC=1.C(OCC)(=O)C.O>[CH2:20]1[O:21][C:9]2([CH2:8][CH:7]([C:3]3[S:4][CH:5]=[CH:6][C:2]=3[Cl:1])[CH2:16][C:15]3[N:14]=[CH:13][CH:12]=[C:11]([CH3:17])[C:10]2=3)[O:18][CH2:19]1

Participants

8

Reactant 4

HCID 174Ethylene GlycolHCID 6101p-Toluenesulfonic acidHCID 516892Sodium BicarbonateHCID 18317361HCID 18317361, compound

Product 1

HCID 18317309HCID 18317309, compoundYield 89.1%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 7-(3-chlorothiophen-2-yl)-4-methyl-5,6,7,8-tetrahydroquinolin-5-one (7.07 g), ethyleneglycol (6.2 g) and p-toluenesulfonic acid (6.9 g) in toluene (200 ml) was refluxed for 15 hours, with separating water, and to the reaction solution were added ethyl acetate (150 ml) and saturated sodium hydrogen carbonate solution (200 ml). The mixture was shaken, and the separated upper layer was washed with water and concentrated under reduced pressure. The residue was purified with silica gel column chromatography to give 7-(3-chlorothiophen-2-yl)-4-methyl-5,6,7,8-tetrahydroquinolin-5-one-ethyleneacetal(7.3 g) as colorless crystals.

Workup

  1. washthe separated upper layer was washed with water
  2. concentrationconcentrated under reduced pressure
  3. customThe residue was purified with silica gel column chromatography

Sources & evidence

ORD record
ord-c6e4000f405d4c00b1bfed1fbdf0f261
Source dataset
uspto-grants-2002_02
Patent number
US06350749B1

Reaction notes

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