1,2-Dichloroethane → HCID 43627454, compound

In a 1 L round-bottomed flask was added 2-amino-3-methylbenzoic acid (11.2 g, 74.1 mmol), N,O-dimethylhydroxylamine hydrochloride (14.45 g, 148 mmol) in CH2Cl2 (500 mL) to give a pale brown suspension. The reaction mixture was treated with Et3N (35 mL) to give a light brown/red solution. The solution was treated with HOBT (11.35 g, 74.1 mmol) and EDC (14.20 g, 74.1 mmol) and stirred at room temperature for 24 hours. The mixture was then washed with 10% LiCl aq acidified with 1N HCl. The organic layer was washed successively with 10% aqueous LiCl and aqueous NaHCO3. The organic layer was decolorized with charcoal, filtered and the filtrate dried over MgSO4. The mixture was filtered and concentrated to give 13.22 g (92% yield) of 2-amino-N-methoxy-N,3-dimethylbenzamide as an oil. MS(ES):m/z=195.1 [M+H+]; HPLC: RT=1.118 min. (H2O/MeOH with TFA, CHROMOLITH® ODS S5 4.6×50 mm, gradient=4 min, wavelength=220 nm); 1H NMR (500 MHz, chloroform-d) δ 7.22 (dd, J=7.8, 0.8 Hz, 1H), 7.12-7.06 (m, 1H), 6.63 (t, J=7.5 Hz, 1H), 4.63 (br. s., 2H), 3.61 (s, 3H), 3.34 (s, 3H), 2.17 (s, 3H). This was used without further purification in next reaction.

1. customto give a pale brown suspension
2. customto give a light brown/red solution
3. washThe mixture was then washed with 10% LiCl aq
4. washThe organic layer was washed successively with 10% aqueous LiCl and aqueous NaHCO3
5. filtrationfiltered
6. dry with materialthe filtrate dried over MgSO4
7. filtrationThe mixture was filtered
8. concentrationconcentrated

ORD record

ord-31a295c8279345d1ba68a4c133db951a

Source dataset

uspto-grants-2015_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09133139B2