Hexane → HCID 10584093, compound

Temperature

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 record

ord-361201ec16604efb92df6ab9e03f34bf

Source dataset

uspto-grants-2015_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09133219B2