Methyl iodide → 1-methyl-5-nitro-2(1H)-pyridinone

Tetra-N-butylammonium bromide (3220 mg, 10.00 mmol), sodium hydroxide (400.0 mg, 10.00 mmol) and methyl iodide (3113 μL, 50.00 mmol) were sequentially added into the two-phase mixture of 2-hydroxy-5-nitropyridine (700.0 mg, 5.000 mmol) in water (25 mL) and methylene chloride (50 mL). The above mixture was stirred at rt for 1 h and then partitioned between CH2Cl2 (50 mL) and water (75 mL). The aqueous layer was extracted with CH2Cl2 (50 mL). The combined organic phases were dried over MgSO4, filtered, and concentrated in vacuo to obtain a beige solid. Silica gel (134 g) was used to purify the above solid eluting with 2500 mL EtOAc to obtain the title compound as beige powder. 1H NMR (CDCl3, 400 MHz): δ=3.66 (s, 3H), 6.57 (d, 1H, J=10.0 Hz), 8.10 (dd, 1H, J=2.8 & 10.0 Hz), 8.63 (d, 1H, J=2.8 Hz). MS (ES+): m/z 155.15 (100) [MH+]. HPLC: tR'1.69 min (ZQ2000, polar—5 min).

1. custompartitioned between CH2Cl2 (50 mL) and water (75 mL)
2. extractionThe aqueous layer was extracted with CH2Cl2 (50 mL)
3. dry with materialThe combined organic phases were dried over MgSO4
4. filtrationfiltered
5. concentrationconcentrated in vacuo
6. customto obtain a beige solid
7. customto purify the above solid
8. washeluting with 2500 mL EtOAc

ORD record

ord-d5e27f3f5afb432ca05f70cf4820b3de

Source dataset

uspto-grants-2008_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07465726B2