Hexane → HCID 10584093, Verbindung

Temperatur

82 °C

Thionyl chloride (10 mL, 137.4 mmol, 4.98 eq) is added at room temperature to a stirred solution of 3,4-dimethoxy-2-nitro-benzoic acid (6.26 g, 27.6 mmol, 1.0 eq) in 1,2-dichloroethane (100 mL). The reaction mixture is heated at 82° C. for 2 hours, then solvent is removed and the resulting crude acid chloride is dissolved in acetone (50 mL), cooled down to 5° C. before the addition of a solution of sodium azide (10.0 g, 154.0 mmol, 5.58 eq) in water (20 mL). After 1 hour stirring, the reaction mixture is poured into water (300 ml), the resulting white precipitate of acyl azide is filtered, washed with water, dissolved in acetic acid (300 mL) and water (30 mL). The mixture is heated at 118° C. for 2 hours, then solvents are evaporated, the residue is taken in warm ethanol and filtered. The filtrate is concentrated and the residue is purified by column chromatography (silica gel, eluent: hexane:ethyl acetate, 10:1 to 5:1, v/v) to afford 3,4-dimethoxy-2-nitro-phenylamine as a red solid (3.5 g, 64% yield).

1. customsolvent is removed
2. dissolutionthe resulting crude acid chloride is dissolved in acetone (50 mL)
3. filtrationthe resulting white precipitate of acyl azide is filtered
4. washwashed with water
5. dissolutiondissolved in acetic acid (300 mL)
6. temperatureThe mixture is heated at 118° C. for 2 hours
7. customsolvents are evaporated
8. filtrationfiltered
9. concentrationThe filtrate is concentrated
10. customthe residue is purified by column chromatography (silica gel, eluent

ORD-Eintrag

ord-dab8a94e4d1b45dd9b5689dcbcb7ae8c

Quelldatensatz

uspto-grants-2015_01

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08927542B2