1,1'-Carbonyldiimidazole → 2-amino-N,6-dimethoxybenzamide

温度

21 °C

A mixture of 2-amino-6-methoxybenzoic acid (4.6 g, 27.52 mmol) and carbonyl-1,1′-dimidazole (5.35 g, 33.02 mmol) in THF (70 ml) was stirred at 21° C. under nitrogen for 3 days. N,N-diisopropyl-N-ethyl-amine (1.667 ml, 9.57 mmol) and O-methylhydroxylaminehydrochloride (0.545 ml, 7.18 mmol) were added. The solution was heated to 50° C. for 3 hours. After cooling and concentration under vacuum, the reaction mixture was diluted with EtOAc, washed with a saturated aqueous solution of sodium hydrogencarbonate, water and brine, dried over magnesium sulfate, concentrated under vacuum. The residue was purified by flash chromatography on silica gel eluting with 10 to 20% EtOAc in DCM to afford 2-amino-N,6-dimethoxybenzamide (318 mg, 33.9%) as a white solid. Mass spectrum: MH+ 197; NMR Spectrum: (DMSOd6) 3.67 (s, 3H), 3.71 (s, 3H), 5.57 (bs, 2H), 6.19 (d, 1H), 6.31 (d, 1H), 7.02 (dd, 1H)

1. temperatureThe solution was heated to 50° C. for 3 hours
2. temperatureAfter cooling
3. concentrationconcentration under vacuum
4. additionthe reaction mixture was diluted with EtOAc
5. washwashed with a saturated aqueous solution of sodium hydrogencarbonate, water and brine
6. dry with materialdried over magnesium sulfate
7. concentrationconcentrated under vacuum
8. customThe residue was purified by flash chromatography on silica gel eluting with 10 to 20% EtOAc in DCM

ORDレコード

ord-4eeda08fd5ba448a9af5234e19039102

出典データセット

uspto-grants-2013_10

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US08569298B2