Diethyl Ether → 1-(1,3-Dioxolan-2-ylmethyl)-7-methoxy-2-oxo-1,2-dihydroquinoline-4-carbaldehyde

HRID 39666Notes

Reaction equation

HRID 39666 reaction equation
C1(C)C(C)=CC=CC=1.[O:9]1[CH2:13][CH2:12][O:11][CH:10]1[CH2:14][N:15]1[C:24]2[C:19](=[CH:20][CH:21]=[C:22]([O:25][CH3:26])[CH:23]=2)[C:18]([CH3:27])=[CH:17][C:16]1=[O:28].C([O:31]CC)C>>[O:9]1[CH2:13][CH2:12][O:11][CH:10]1[CH2:14][N:15]1[C:24]2[C:19](=[CH:20][CH:21]=[C:22]([O:25][CH3:26])[CH:23]=2)[C:18]([CH:27]=[O:31])=[CH:17][C:16]1=[O:28]

Participants

4

Reactant 3

HCID 3283Diethyl EtherHCID 7237O-XyleneHCID 593980471-(1,3-dioxolan-2-ylmethyl)-7-methoxy-4-methylquinolin-2(1H)-one

Product 1

HCID 593978441-(1,3-Dioxolan-2-ylmethyl)-7-methoxy-2-oxo-1,2-dihydroquinoline-4-carbaldehyde

Conditions

Temperature
60 °C

Procedure

To 3 mL of a xylene solution containing 50 mg of 1-(1,3-dioxolan-2-ylmethyl)-7-methoxy-4-methylquinolin-2(1H)-one, 20 mg of serene dioxide was added, and the mixture was stirred for 6 hours under reflux. The reaction mixture was cooled to 60° C., the insoluble material filtered off, and the filtration residue was washed with chloroform. The filtrate and the washing solution were combined, and the solvent was removed under reduced pressure. The residue thus obtained was added with diethyl ether, and a solid substance was collected by filtration to obtain a yellow solid, 34 mg of 1-(1,3-dioxolan-2-ylmethyl)-7-methoxy-2-oxo-1,2-dihydroquinoline-4-carbaldehyde.

Workup

  1. additionwas added
  2. temperatureunder reflux
  3. filtrationthe insoluble material filtered off
  4. washthe filtration residue was washed with chloroform
  5. customthe solvent was removed under reduced pressure
  6. customThe residue thus obtained
  7. filtrationa solid substance was collected by filtration

Sources & evidence

ORD record
ord-40b3f1e7cd594c03920becb70f7b2bd4
Source dataset
uspto-grants-2013_09
Patent number
US08524738B2

Reaction notes

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