5-Bromo-2-methyl-3-nitropyridine → 5-Bromo-2-methylpyridin-3-amine

To a solution of 5-bromo-2-methyl-3-nitro-pyridine (stage 75.1.5, 765 mg, 3.53 mmol) in acetic acid (7 ml) and water (1.75 ml) was added in three portions iron powder (591 mg, 10.6 mmol). The reaction mixture was stirred for 2.5 h at rt then quenched with 20 ml of 10 M aqueous NaOH, 20 g ice and 20 ml EtOAc before being filtered over Celite. The solid was washed with EtOAc and the filtrate was extracted with EtOAc. The combined organic layers were washed with brine, dried over Na2SO4, filtered and evaporated to give the title compound as a gray solid. (HPLC: tR 1.52 min (Method A); M+H=187, 189 MS-ES).

1. customthen quenched with 20 ml of 10 M aqueous NaOH, 20 g ice and 20 ml EtOAc
2. filtrationbefore being filtered over Celite
3. washThe solid was washed with EtOAc
4. extractionthe filtrate was extracted with EtOAc
5. washThe combined organic layers were washed with brine
6. dry with materialdried over Na2SO4
7. filtrationfiltered
8. customevaporated

ORD record

ord-1dd6cd9d18c1487e851baa01ff8114c0

Source dataset

uspto-grants-2013_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08476294B2