Water → N-(2-Methoxy-phenyl)-malonamic acid

To a solution of 2-methoxybenzeneamine (1.1 g, 8.93 mmol) in DCM (90 mL) was added TMSCl (1.1 mL, 8.93 mmol) at room temperature [Rigo, B.; Fasseur, D.; Cauliez, P. and Couturier, D. Tetrahedron Lett.; 30; 23; 1989; 3073-3076.]. The reaction mixture was stirred for 30 mins before the addition of 2,2-dimethyl-1,3-dioxane-4,6-dione (1.29 g, 8.93 mmol) and then stirring was continued mixture for additional 2 hours. Water (1 mL) was added, and the reaction mixture was concentrated under reduced pressure. The residue was poured into saturated NaHCO3 solution, and extracted with EtOAc. The aqueous phase was collected, acidified with conc. HCl to pH˜4, extracted with EtOAc, the extract was dried over anhydrous Na2SO4 and concentrated. The residue was purified by flash chromatography (eluent CHCl3/MeOH/AcOH 9:1:0.1) to afford the compound 27 (0.56 g, 30% yield) as a white solid. 1H NMR (DMSO-d6) δ (ppm): 12.62 (bs, 1H), 9.52 (s, 1H), 8.02 (dd, 1H), 7.03 (m, 2H), 6.88 (m, 1H), 3.82 (s, 3H), 3.46 (s, 2H). MS (m/z): 210.1 (M+H).

1. customfor additional 2 hours
2. concentrationthe reaction mixture was concentrated under reduced pressure
3. additionThe residue was poured into saturated NaHCO3 solution
4. extractionextracted with EtOAc
5. customThe aqueous phase was collected
6. extractionextracted with EtOAc
7. dry with materialthe extract was dried over anhydrous Na2SO4
8. concentrationconcentrated
9. customThe residue was purified by flash chromatography (eluent CHCl3/MeOH/AcOH 9:1:0.1)

ORD record

ord-9e0c3875a754494b8caf65e52f62733f

Source dataset

uspto-grants-2012_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08329726B2