6-Methoxy-7-(2-methoxyvinyl)quinoline → (6-Methoxyquinolin-7-yl)acetaldehyde

HRID 494968Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[CH:13]=[CH:14][O:15]C)[N:9]=[CH:8][CH:7]=[CH:6]2>Cl.O1CCCC1.C(OCC)(=O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[CH2:13][CH:14]=[O:15])[N:9]=[CH:8][CH:7]=[CH:6]2

Participants

Conditions

Temperature: 70 °C

Procedure

1.41 g of 6-methoxy-7-(2-methoxyvinyl)quinoline was dissolved in 40 ml of 2 N hydrochloric acid-tetrahydrofuran (1:1), and the obtained mixture was then stirred at 70° C. for 2 hours. The reaction solution was cooled to a room temperature. It was diluted with ethyl acetate and then washed with a saturated sodium bicarbonate aqueous solution and a saturated sodium chloride aqueous solution. The organic layer was dried over magnesium sulfate and then concentrated under a reduced pressure, so as to obtain 1.45 g of (6-methoxyquinolin-7-yl)acetaldehyde containing triphenylphosphine oxide. This compound was used in the following reaction without further purification.

Workup

temperatureThe reaction solution was cooled to a room temperature
washwashed with a saturated sodium bicarbonate aqueous solution
dry with materialThe organic layer was dried over magnesium sulfate
concentrationconcentrated under a reduced pressure

Sources & evidence

ORD record: ord-d1df36b1c4154fa78c2805b98af415f7
Source dataset: uspto-grants-2009_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07538123B2

Reaction notes

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