Iodine → 3-Ethyl-8-methoxyquinoline
Reaction equation
[CH2:1]([C:3](=[CH2:6])[CH:4]=O)[CH3:2].[CH3:7][O:8][C:9]1[C:10]([NH2:15])=[CH:11][CH:12]=[CH:13][CH:14]=1.II.[OH-].[Na+]>S(=O)(=O)(O)O>[CH2:1]([C:3]1[CH:4]=[N:15][C:10]2[C:11]([CH:6]=1)=[CH:12][CH:13]=[CH:14][C:9]=2[O:8][CH3:7])[CH3:2]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 110 °C
Procedure
Freshly distilled 2-ethyl acrolein (1.7 ml) was added, over 20 minutes, to a solution of o-anisidine (1.5 g) and iodine (20 mg) in 70% sulphuric acid (10 ml) stirring at 110° C. After 2 hours the reaction was cooled to 0° C. and basified with 25% aqueous sodium hydroxide (pH 13). The aqueous layer was extracted with ethyl acetate (2×100 ml) and the extracts combined. The organic layer was extracted with 2M hydrochloric acid (2×100 ml) and the combined acidic extracts basified once again with 25% sodium hydroxide. The aqueous layer was extracted with ethyl acetate (2×100 ml), the extracts combined, dried over magnesium sulphate, filtered, and the filtrate evaporated in vacuo. The residue was purified by column chromatography, eluting with 25%-50% ethyl acetate in hexane, to yield the title product as a tan oil (0.42 g).
Workup
- temperatureAfter 2 hours the reaction was cooled to 0° C.
- extractionThe aqueous layer was extracted with ethyl acetate (2×100 ml)
- extractionThe organic layer was extracted with 2M hydrochloric acid (2×100 ml)
- extractionThe aqueous layer was extracted with ethyl acetate (2×100 ml)
- dry with materialdried over magnesium sulphate
- filtrationfiltered
- customthe filtrate evaporated in vacuo
- customThe residue was purified by column chromatography
- washeluting with 25%-50% ethyl acetate in hexane
Sources & evidence
- ORD record
- ord-21b152ec0edc4f689a5c710dd5d7bab5
- Source dataset
- uspto-grants-1998_09
- Patent number
- US05804588
Reaction notes
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