Ethylene Glycol → HCID 66596793, compound

HRID 1811401Notes

Reaction equation

HRID 1811401 reaction equation
[CH3:1][O:2][C:3]1[C:12]2[NH:11][C:10](=[O:13])[CH2:9][CH2:8][C:7]=2[C:6]([CH:14]=[O:15])=[CH:5][CH:4]=1.[CH2:16](O)[CH2:17][OH:18].C(=O)(O)[O-].[Na+]>C1(C)C=CC=CC=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>[O:15]1[CH2:16][CH2:17][O:18][CH:14]1[C:6]1[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[C:12]2[C:7]=1[CH2:8][CH2:9][C:10](=[O:13])[NH:11]2

Participants

6

Reactant 3

HCID 174Ethylene GlycolHCID 516892Sodium BicarbonateHCID 859802658-Methoxy-2-oxo-1,2,3,4-tetrahydroquinoline-5-carboxaldehyde

Product 1

HCID 66596793HCID 66596793, compoundYield 70%

Reagents, catalysts & solvents 2

HCID 521998p-Toluenesulfonic acid monohydrateCatalystHCID 1140TolueneSolvent

Procedure

8-Methoxy-2-oxo-1,2,3,4-tetrahydroquinoline-5-carboxaldehyde (42 g) was suspended in toluene (400 ml), and ethylene glycol (33.7 ml) and p-toluenesulfonic acid monohydrate (0.78 g) were added, and the resulting mixture was heated under reflux in a Dean-Stark apparatus for 4.5 hours. The reaction mixture was cooled, and 10 ml of an aqueous solution containing 1.72 g of sodium bicarbonate was added. Stirring was carried out for some time, and the produced solid was collected by filtration. The solid was washed with water and toluene and dried at 60° C. to thereby obtain 35.5 g (yield: 70%) of 5-(1,3-dioxolan-2-yl)-8-methoxy-3,4-dihydro-1H-quinolin-2-one as white crystals.

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureunder reflux in a Dean-Stark apparatus for 4.5 hours
  3. temperatureThe reaction mixture was cooled
  4. additionwas added
  5. filtrationthe produced solid was collected by filtration
  6. washThe solid was washed with water and toluene
  7. customdried at 60° C.

Sources & evidence

ORD record
ord-f07a3071184d4addbe522c12e99b72ac
Source dataset
uspto-grants-2013_01
Patent number
US08362252B2

Reaction notes

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