Trimethylsilyldiazomethane → HCID 67083635, Verbindung

Temperatur

0 °C

To a suspension of 4-amino-2-chloro-3-methyl-benzoic acid (0.64 g, 3.45 mmol) in toluene (10 mL) and methanol (10 mL) at 0° C. was added drop-wise trimethylsilyldiazomethane (3.45 mL, 2 M in hexane, 6.90 mmol). The reaction mixture was stirred at 0° C. for 30 min during which the reagents dissolved. The reaction mixture was quenched by the addition of acetic acid (1 mL) then washed with aqueous saturated sodium bicarbonate solution (10 mL) and the aqueous fraction extracted twice with ethyl acetate (2×10 mL). The combined organic extracts were washed with brine (20 mL), dried (MgSO4) and concentrated in vacuo to give the title compound as a beige solid (0.66 g, 96%). 1H NMR (CDCl3, 400 MHz) 2.26 (3H, s), 3.86 (3H, s), 6.55 (1H, d, J=8.8 Hz), 7.60 (1H, d, J=8.8 Hz).

1. dissolutiondissolved
2. customThe reaction mixture was quenched by the addition of acetic acid (1 mL)
3. washthen washed with aqueous saturated sodium bicarbonate solution (10 mL)
4. extractionthe aqueous fraction extracted twice with ethyl acetate (2×10 mL)
5. washThe combined organic extracts were washed with brine (20 mL)
6. dry with materialdried (MgSO4)
7. concentrationconcentrated in vacuo

ORD-Eintrag

ord-7f7a80a5505b4ab7a3cff63c42703a42

Quelldatensatz

uspto-grants-2014_09

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08841462B2