Dimethylformamide → 2-Quinolinemethanol

温度

60 °C

A mixture of 2-chloromethylquinoline hydrochloride (21.4 g), sodium acetate (32.8 g) and N,N-dimethylformamide (200 ml) was stirred at 60° C. overnight. After cooling, the reaction solution was poured into water, which was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated aqueous sodium chloride solution, dried (MgSO4), and concentrated. A mixture of the residue, 4N aqueous sodium hydroxide solution (50 ml), tetrahydrofuran (100 ml) and methanol (100 ml) was stirred at room temperature for 1 hour, and poured into water, which was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated aqueous sodium chloride solution, dried (MgSO4) and concentrated. The residue was subjected to silica gel column chromatography to obtain 2-quinolylmethanol (14.0 g, yield 88%) as colorless crystals from the fraction eluted with ethyl acetate-hexane (1:2, volume ratio). This was recrystallized from ethyl acetate-hexane. Melting point: 68–69° C.

1. temperatureAfter cooling
2. extractionwas extracted with ethyl acetate
3. washThe ethyl acetate layer was washed with saturated aqueous sodium chloride solution
4. dry with materialdried (MgSO4)
5. concentrationconcentrated
6. additionA mixture of the residue, 4N aqueous sodium hydroxide solution (50 ml), tetrahydrofuran (100 ml) and methanol (100 ml)
7. stirringwas stirred at room temperature for 1 hour
8. additionpoured into water, which
9. extractionwas extracted with ethyl acetate
10. washThe ethyl acetate layer was washed with saturated aqueous sodium chloride solution
11. dry with materialdried (MgSO4)
12. concentrationconcentrated

ORDレコード

ord-67c2609613714934a148a2d0bb458683

出典データセット

uspto-grants-2007_02

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US07179823B1