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0 °C

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′).

1. customTo a 25 mL round-bottomed flask equipped with a magnetic stirrer and under a N2 (g)
2. custompurge
3. stirringthe resulting mixture was stirred for 6 h
4. customto quenching
5. customthe reaction with 50% NaOH until the pH was ca. 10
6. filtrationThe brown solution was filtered through a pad of celite
7. extractionextracted with methylene chloride (4×15 mL)
8. washThe combined organic phases were washed with water (20 mL), brine (15 mL)
9. dry with materialdried (NaSO4)
10. concentrationconcentrated in-vacuo
11. customto afford a brown solid that
12. customwas purified by Combiflash (0 to 60% ethyl acetate in hexanes over 30 min)