Epichlorohydrin → 5-(Oxiran-2-ylmethoxy)quinoline
Reaction equation
[OH:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2.[H-].[Na+].[CH2:14]([CH:16]1[O:18][CH2:17]1)Cl>CN(C)C=O>[O:18]1[CH2:17][CH:16]1[CH2:14][O:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 50 °C
Procedure
83 g of 5-hydroxyquinoline were dissolved in 1.5 l of dried dimethylformamide (DMF), and, after adding 23.3 g of sodium hydride (content: 60% ), the resulting mixture was stirred with heating at 50° C. for 30 minutes. 160 g of epichlorohydrin were added to the reaction mixture, and, after stirring with heating at 90° C. for 3 hours, the solvent was evaporated off under reduced pressure. Water was added to the resulting residue and extracted with chloroform. The chloroform extract was decolorized and purified with active carbon, dried with anhydrous mirabilite and then evaporated. The residue was purified by column chromatography on silica gel. 71 g of the targeted 5-(2,3-epoxypropoxy)quinoline were obtained as an oily substance by chromatography using a solvent mixture of chloroform:methanol=100:1 (volume ratio)for elution.
Workup
- stirringafter stirring
- temperaturewith heating at 90° C. for 3 hours
- customthe solvent was evaporated off under reduced pressure
- additionWater was added to the resulting residue
- extractionextracted with chloroform
- extractionThe chloroform extract
- custompurified with active carbon
- dry with materialdried with anhydrous mirabilite
- customevaporated
- customThe residue was purified by column chromatography on silica gel
Sources & evidence
- ORD record
- ord-6ac9a67cf2194692bc4baeb152541743
- Source dataset
- uspto-grants-1995_07
- Patent number
- US05434155
Reaction notes
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