1-Butanol → 4-Butoxy-quinoline-6-carbaldehyde

HRID 853008Notes

Reaction equation

C(N=[CH:6][C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][CH:16]=1)[N:13]=[CH:12][CH:11]=[C:10]2Cl)CCC.[O-:18][CH2:19][CH2:20][CH2:21][CH3:22].[Na+].C([OH:28])CCC>Cl>[CH2:19]([O:18][C:10]1[C:9]2[C:14](=[CH:15][CH:16]=[C:7]([CH:6]=[O:28])[CH:8]=2)[N:13]=[CH:12][CH:11]=1)[CH2:20][CH2:21][CH3:22]

Participants

Conditions

Temperature: 120 °C

Procedure

A mixture of butyl (4-chloro-quinolin-6-ylmethylene)-amine (322 mg, 1.3 mmol) and a solution of sodium butoxide in butanol (3 mL, 6.0 mmol, 2.0M) were placed in a microwave tube and the mixture was heated to 120° C. for 30 min in a closed microwave. Then, the suspension was diluted with 3.0N hydrochloric acid (3 mL) and the solvent was removed under the vacuum. The residue was diluted with water and the organic compound was extracted into ethyl acetate (3×50 mL). The combined extracts were washed with saturated sodium bicarbonate solution, brine solution and dried over anhydrous magnesium sulfate. After filtration of the drying agent, the solvent was removed under the vacuum and the residue was purified by using a Biotage silica gel column chromatography to obtain 145 mg (48.5% yield) of 4-butoxy-quinoline-6-carbaldehyde as a white solid: EI-LRMS m/e calcd for C14H15NO2 (M+) 230.1, found 230.1.

Workup

customthe solvent was removed under the vacuum
additionThe residue was diluted with water
extractionthe organic compound was extracted into ethyl acetate (3×50 mL)
washThe combined extracts were washed with saturated sodium bicarbonate solution, brine solution
dry with materialdried over anhydrous magnesium sulfate
filtrationAfter filtration of the drying agent
customthe solvent was removed under the vacuum
customthe residue was purified

Sources & evidence

ORD record: ord-32762b601f294bf0a785b9cb5a2317b0
Source dataset: uspto-grants-2007_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07253285B2

Reaction notes

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