Salicylaldehyde → (E)-2-(2-(Quinolin-2-yl)prop-1-enyl)phenyl Acetate
Reaction equation
[CH2:1]([C:3]1[CH:12]=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]=1)[CH3:2].[OH:13][C:14]1[CH:21]=[CH:20][CH:19]=[CH:18][C:15]=1[CH:16]=O.[C:22](OC(=O)C)(=[O:24])[CH3:23]>>[C:22]([O:13][C:14]1[CH:21]=[CH:20][CH:19]=[CH:18][C:15]=1/[CH:16]=[C:1](/[C:3]1[CH:12]=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]=1)\[CH3:2])(=[O:24])[CH3:23]Participants
Conditions
- Temperature
- 150 °C
Procedure
2-Ethylquinoline (1.57 g, 10.0 mmol, 1.0 eq.) and 2-hydroxybenzaldehyde (1.06 mL, 1.22 g, 10.0 mmol, 1.0 eq.) were dissolved in acetic anhydride (1.89 mL, 2.04 g, 20.0 mmol, 2.0 eq.). The resulting mixture was heated at 150° C. for 16 h. The mixture was allowed to cool down to r.t. and was poured onto water (100 mL) and was stirred vigorously. The mixture was extracted with ethyl acetate (3×30 mL). The combined organic extracts were washed with brine (25 mL), dried over sodium sulfate and concentrated under reduced pressure which gave the crude product (3.63 g) as a clear orange oil. The crude product was purified by column chromatography (SiO2, 1:5 ethyl acetate-cyclohexane) twice, which yielded the product (2.22 g, 73% yield) as a clear colourless oil.
Workup
- temperatureto cool down to r.t.
- additionwas poured onto water (100 mL)
- extractionThe mixture was extracted with ethyl acetate (3×30 mL)
- washThe combined organic extracts were washed with brine (25 mL)
- dry with materialdried over sodium sulfate
- concentrationconcentrated under reduced pressure which
- customgave the crude product (3.63 g) as a clear orange oil
- customThe crude product was purified by column chromatography (SiO2, 1:5 ethyl acetate-cyclohexane) twice
Sources & evidence
- ORD record
- ord-da2ee3581e304baa96009539acfc7809
- Source dataset
- uspto-grants-2016_07
- Patent number
- US09388138B2
Reaction notes
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