反应 #89711

反应方程式

hydroxylamine-O-sulfonic acid

quinaldine

methanol

sulfuric acid

→

4-hydroxymethyl-2-methyl quinoline

收率 52.0%

溶剂

water

反应条件

后处理

1. 1
   其他To a 25 mL round-bottomed flask equipped with a magnetic stirrer and under a N2 (g)
2. 2
   其他purge
3. 3
   workup.STIRRINGthe resulting mixture was stirred for 6 h
4. 4
   其他to quenching
5. 5
   其他the reaction with 50% NaOH until the pH was ca. 10
6. 6
   过滤The brown solution was filtered through a pad of celite
7. 7
   萃取extracted with methylene chloride (4×15 mL)
8. 8
   洗涤The combined organic phases were washed with water (20 mL), brine (15 mL)
9. 9
   干燥dried (NaSO4)
10. 10
    浓缩concentrated in-vacuo
11. 11
    其他to afford a brown solid that
12. 12
    其他was purified by Combiflash (0 to 60% ethyl acetate in hexanes over 30 min)

实验过程

To a 25 mL round-bottomed flask equipped with a magnetic stirrer and under a N2 (g) purge was placed sequentially: quinaldine (0.57 g, 4.0 mmol), methanol (8 mL), and water (4 mL). The solution was cooled to 0° C. prior to the sequential addition of: concentrated sulfuric acid (0.2 mL, 4 mmol), iron (II) sulfate heptahydrate (0.33 g, 1.2 mmol), and iron powder (0.067 g, 1.2 mmol). After stirring the heterogeneous mixture for 10 min, hydroxylamine-O-sulfonic acid (HOSA) (1.36 g, 12 mmol) was added and the resulting mixture was stirred for 6 h prior to quenching the reaction with 50% NaOH until the pH was ca. 10. The brown solution was filtered through a pad of celite and then extracted with methylene chloride (4×15 mL). The combined organic phases were washed with water (20 mL), brine (15 mL), dried (NaSO4), and concentrated in-vacuo to afford a brown solid that was purified by Combiflash (0 to 60% ethyl acetate in hexanes over 30 min) to afford 360 mg (52%) of pure 4-hydroxymethyl-2-methyl quinoline. LCMS (ESI): 174 (M+H′).

来源