2-Methyl-3-nitro-5-(trifluoromethyl)pyridine → 2-Methyl-5-(trifluoromethyl)pyridin-3-amine

2-Methyl-3-nitro-5-(trifluoromethyl)pyridine (51 mg, 0.247 mmol) and 10% Pd/C, (50% wet, 10 mg, 4.70 μmol) in EtOH (10 mL) were combined in a Parr hydrogenation flask. The reaction mixture was purged of air under vacuum and pressurized with hydrogen (33 psi). The flask was shaken for 18 h. An additional portion of 10% Pd/C, (50% wet, 20 mg, 9.40 μmol) was added and the mixture was hydrogenated (40 psi) overnight. The reaction mixture was filtered through Celite® and the filter cake was washed with EtOH. The combined filtrate and washings were concentrated in vacuo and purified by silica gel chromatography to provide 2-methyl-5-(trifluoromethyl)pyridin-3-amine (17 mg, 399% yield). 1H NMR (400 MHz, DMSO-d6): δ 7.93 (s, 1 H), 7.13 (s, 1H), 5.56 (s, 2 H), 2.31 (s, 3 H); MS (ESI) m/z; 177.0 (M+H+).

1. customThe reaction mixture was purged of air under vacuum
2. additionAn additional portion of 10% Pd/C, (50% wet, 20 mg, 9.40 μmol) was added
3. custom(40 psi) overnight
4. filtrationThe reaction mixture was filtered through Celite®
5. washthe filter cake was washed with EtOH
6. concentrationThe combined filtrate and washings were concentrated in vacuo
7. custompurified by silica gel chromatography

ORD record

ord-c3dcd14d4e4a481281320913d5c20d78

Source dataset

uspto-grants-2012_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08143293B2