Ammonia → 2-Hydroxy-6-methoxy-3-nitropyridine

Temperature

-78 °C

To a cooled suspension of Na t-OBu (6.24 g, 64.9 mmol) in liquid ammonia was added dropwise a solution of 6-methoxy-3-nitropyridine (2.0 g, 12.98 mmol) and t-butyl hydrogenperoxide (1.53 mL, 14.31 mmol) in THF (20 mL). After the completion of addition, the resulting mixture was stirred at −78° C. under Ar and warmed gradually to room temperature, and then stirred at room temperature overnight, which gave a yellow solid. It was diluted with H2O (30 mL). The resulting mixture was neutralized with the addition of 1N HCl solution. The solid formed was collected and washed with H2O and DCM, and then dried (1.18 g). The filtrate was extracted with DCM (2×20 mL). The combined organic layers were dried (MgSO4), filtered and concentrated to give the second portion (0.59 g, total 1.77 g, 80%). NMR (MeOD-d3, 400 MHz) □ 8.20 (d, J=8.8 Hz, 1H), 5.79 (d, J=8.8 Hz, 1H), 4.87 (s, 3H). MS: m/z=171 (M+H+).

1. additionAfter the completion of addition
2. temperaturewarmed gradually to room temperature
3. stirringstirred at room temperature overnight
4. customwhich gave a yellow solid
5. customThe solid formed
6. customwas collected
7. washwashed with H2O and DCM
8. customdried (1.18 g)
9. extractionThe filtrate was extracted with DCM (2×20 mL)
10. dry with materialThe combined organic layers were dried (MgSO4)
11. filtrationfiltered
12. concentrationconcentrated
13. customto give the second portion (0.59 g, total 1.77 g, 80%)

ORD record

ord-6af7afe636f44c87a85772dc8f320b3a

Source dataset

uspto-grants-2013_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08420052B2