Acetate → (5-Methoxy-4-nitropyridin-2-yl)methanol

Temperature

150 °C

5-Methoxy-2-methyl-4-nitropyridine 1-oxide (7 g, 0.038 mol) was dissolved in acetic anhydride (70 mL, Sdfine, India) and the resulting solution was stirred for 3 h at 150° C. The reaction mixture was concentrated and Et2O (250 mL) was added to the residue and it was neutralized with sat'd NaHCO3 (100 mL). The organic layer was separated and dried over anhydrous sodium sulfate, concentrated to afford a pale yellow solid which was dissolved in MeOH and THF (100 mL) and treated with LiOH (2.73 g, 0.113 mol). The reaction mixture was stirred for 2 h at rt. The progress of the reaction was monitored by TLC (5% MeOH in CHCl3). After completion of acetate hydrolysis, sat NH4Cl (20 mL) was added and the product was extracted with EtOAc. The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure to afford the title compound as an off white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 8.71 (s, 1H), 7.81 (s, 1H), 5.62 (t, J=5.7 Hz, 1H), 4.59 (d, J=6 Hz, 2H), 4.04 (s, 3H). MS (ESI, positive ion) m/z: 185.1 (M+H).

1. concentrationThe reaction mixture was concentrated
2. additionEt2O (250 mL) was added to the residue and it
3. customThe organic layer was separated
4. dry with materialdried over anhydrous sodium sulfate
5. concentrationconcentrated
6. customto afford a pale yellow solid which
7. stirringThe reaction mixture was stirred for 2 h at rt
8. additionwas added
9. extractionthe product was extracted with EtOAc
10. dry with materialThe organic layer was dried over anhydrous sodium sulfate
11. concentrationconcentrated under reduced pressure

ORD record

ord-9199e7c6c5d64ba3b9fc7e6f1d5b3279

Source dataset

uspto-grants-2014_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08710043B2