Methylamine → 2-Amino-3-fluoro-n-methylbenzamide

1,1′-Carbonyldiimidazole (1.946 g, 12.00 mmol) was added in one portion to 2-amino-3-fluorobenzoic acid (1.551 g, 10 mmol) in THF (25 mL) at room temperature and the resulting suspension stirred for 18 hours. A 2N solution of methylamine in THF (7.50 mL, 15.00 mmol) was added and the resulting solution stirred at room temperature for 1 hour. The mixture was evaporated and the residue dissolved in EtOAc (100 mL). The solution was washed sequentially with water (2×50 mL) and a saturated solution of NaCl (50 mL). The organic layer was dried over MgSO4 and then evaporated. The residue was dissolved in EtOAc (100 mL) and the mixture washed sequentially with a 2M solution of NaOH (50 mL), water (50 mL), and then with a saturated solution of NaCl (50 mL). The organic layer was dried over MgSO4 and then evaporated to afford 2-amino-3-fluoro-N-methylbenzamide (1.349 g, 80% yield); 1H NMR spectrum: (300 MHz, CDCl3) δ 2.91 (3H, d), 5.52 (2H, s), 5.97 (1H, s), 6.49 (1H, td), 6.93-7.04 (2H, m); Mass spectrum: m/z (ESI+) (M+H)+ =169.34.

1. stirringthe resulting solution stirred at room temperature for 1 hour
2. customThe mixture was evaporated
3. dissolutionthe residue dissolved in EtOAc (100 mL)
4. washThe solution was washed sequentially with water (2×50 mL)
5. dry with materialThe organic layer was dried over MgSO4
6. customevaporated
7. dissolutionThe residue was dissolved in EtOAc (100 mL)
8. washthe mixture washed sequentially with a 2M solution of NaOH (50 mL), water (50 mL)
9. dry with materialThe organic layer was dried over MgSO4
10. customevaporated

ORD record

ord-03d4002386b94d60bc11b4335b59f22f

Source dataset

uspto-grants-2013_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08569298B2