Methylamine → 2-Amino-4-chloro-N-methylbenzamide

Carbonyl-1,1′-diimidazole (1.70 g) was added to 2-amino-4-chlorobenzoic acid (1.50 g) in THF (22.2 mL). After stirring overnight a solution of methylamine in THF (2M, 6.6 mL) was added and the reaction stirred for 3 hours. The reaction was concentrated in vacuo and the residue dissolved in EtOAc (100 mL) and saturated aqueous sodium bicarbonate solution (50 mL). The organics were then washed with saturated aqueous sodium bicarbonate solution (50 mL) and then water (2×100 mL). The organics were extracted with 1 M HCl (4×25 mL, then 2×100 mL then 50 mL), the aqueous phase basified with potassium carbonate (˜50 g) and the organics discarded. The aqueous was then extracted with EtOAc (2×50 mL). The combined organics were dried (MgSO4, 10 g) and concentrated to give 2-amino-4-chloro-N-methylbenzamide (1.2 g, 74%).

1. additionwas added
2. concentrationThe reaction was concentrated in vacuo
3. dissolutionthe residue dissolved in EtOAc (100 mL)
4. washThe organics were then washed with saturated aqueous sodium bicarbonate solution (50 mL)
5. extractionThe organics were extracted with 1 M HCl (4×25 mL
6. extractionThe aqueous was then extracted with EtOAc (2×50 mL)
7. dry with materialThe combined organics were dried (MgSO4, 10 g)
8. concentrationconcentrated

ORD record

ord-23fc722cfcc24f598c2a0eb96ea7dfa3

Source dataset

uspto-grants-2013_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08569298B2