2,3-Dimethyl 2,3-pyridinedicarboxylate → (Pyridine-2,3-diyl)dimethanol--hydrogen chloride (1/1)

温度

5 °C

To a solution of pyridine-2,3-dicarboxylic acid dimethyl ester (25.0 g, 128.1 mmol) in ethanol (183 mL) was added sodium borohydride (24.2 g, 640.5 mmol). The resulting mixture was cooled to 5° C. while stirring under argon. A solution of calcium chloride (12.6 g, 113.5 mmol) in ethanol (77 mL) was added dropwise while maintaining a temperature between 10° C. and 15° C. After addition, the resulting mixture was allowed to warm to room temperature over 16 h. A mixture of 4:1 water/ethanol (100 mL) added and the resulting mixture stirred 1 hr, then evaporated in vacuo to yield a white solid, which was finely ground with mortar and pestle. The fine powder was refluxed for 3 h in ethanol (450 mL), cooled to room temperature and filtered through dicalite. The filtrate was filtered through Nylon 66, 0.45-μ filter, then treated with anhydrous hydrogen chloride gas until solution was pH 2 while cooling on ice bath. A white precipitate was isolated and washed with ethyl ether and dried to yield (2-hydroxymethyl-pyridin-3-yl)-methanol hydrogen chloride as a white solid. C7H9NO2; MS (ESI) m/z 140.1 (MH)+.

1. temperaturewhile maintaining a temperature between 10° C. and 15° C
2. additionAfter addition
3. temperatureto warm to room temperature over 16 h
4. additionadded
5. stirringthe resulting mixture stirred 1 hr
6. customevaporated in vacuo
7. customto yield a white solid, which
8. temperaturecooled to room temperature
9. filtrationfiltered through dicalite
10. filtrationThe filtrate was filtered through Nylon 66, 0.45-μ filter
11. additiontreated with anhydrous hydrogen chloride gas until solution
12. temperaturewhile cooling on ice bath
13. customA white precipitate was isolated
14. washwashed with ethyl ether
15. customdried

ORDレコード

ord-964d4ce26f674defa31a85a47a61c06d

出典データセット

uspto-grants-2014_03

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US08673890B2