Methyl iodide → Methyl 3-methylanthranilate

To a solution of 2-amino-3-methylbenzoic acid (10.1 g, 66.9 mmol) in N,N-dimethylformamide (200 mL) was added cesium carbonate (33.2 g, 102 mmol, 1.5 eq). The mixture was stirred for 30 min. A solution of methyl iodide (4.17 mL, 67.0 mmol, 1.0 eq) in N,N-dimethylformamide (50 mL) was added dropwise and the reaction mixture was maintained for 18 h at rt. The reaction mixture was partitioned between water (1 L) and ether (200 mL) and the water layer was extracted with an additional volume of ether (100 mL). The combined extracts were washed with brine (500 mL), dried over anhydrous potassium carbonate, and concentrated to provide 10.2 g (92%) of methyl 2-amino-3-methylbenzoate, 1H NMR (400 MHz, CDCl3) δ 7.77 (d, 1H), 7.19 (d, 1H), 6.59 (t, 1H), 5.82 (bs, 2H), 3.86 (s, 3H), 2.17 (s, 3H).

1. customThe reaction mixture was partitioned between water (1 L) and ether (200 mL)
2. extractionthe water layer was extracted with an additional volume of ether (100 mL)
3. washThe combined extracts were washed with brine (500 mL)
4. dry with materialdried over anhydrous potassium carbonate
5. concentrationconcentrated

ORD record

ord-315cc1461adc44ad909043f266514bf4

Source dataset

uspto-grants-2012_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08252811B2