Ethylene Glycol → HCID 66596793, compound

HRID 503992Notes

Reaction equation

HRID 503992 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-1e2553d19e084690b34f86c8bec65b9a
Source dataset
uspto-grants-2010_08
Patent number
US07777038B2

Reaction notes

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