Trimethylsilyldiazomethane → Methyl 2-amino-4-methoxybenzoate

To a solution of 4-methoxyanthranilic acid (5.0 g, 30.0 mmol) in a mixture of 10% methanol in tetrahydrofuran (100 mL) was added dropwise (trimethylsilyl)diazomethane (2.0 M solution in diethyl ether, 18.0 mL, 36.0 mmol) at 0° C. The reaction mixture was stirred for 16 hours at room temperature then quenched by the addition of glacial acetic acid (0.1 mL). The reaction mixture was concentrated and the residue was partitioned between saturated sodium bicarbonate (50 mL) and ethyl acetate (250 mL). The organic layer was separated and washed with water (50 mL), saturated sodium bicarbonate (50 mL) and brine (50 mL), dried over sodium sulfate, filtered and concentrated to give methyl 2-amino-4-methoxybenzoate as an oil (5.4 g, quantitative). MS (EI) for C9H11NO3: 182 (MH+).

1. customthen quenched by the addition of glacial acetic acid (0.1 mL)
2. concentrationThe reaction mixture was concentrated
3. customthe residue was partitioned between saturated sodium bicarbonate (50 mL) and ethyl acetate (250 mL)
4. customThe organic layer was separated
5. washwashed with water (50 mL), saturated sodium bicarbonate (50 mL) and brine (50 mL)
6. dry with materialdried over sodium sulfate
7. filtrationfiltered
8. concentrationconcentrated

ORD-Eintrag

ord-f743523be02a438aa262fe6cef8e59c1

Quelldatensatz

uspto-grants-2014_02

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08648066B2