Diisopropylethylamine → HCID 19068877, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 4,5-dimethyl-6-iodo-2-nitroaniline (17.52 g, 60 mmol), bis(triphenylphosphine)palladium (II) chloride (1.75 g) and ethyldiisopropylamine (11.5 mL, 66 mmol) in tetrahydofuran/methanol (1:1, 300 mL) was heated at 100° C. under a carbon monoxide atmosphere (100 psi, 6.7 atm) in an autoclave for 8 hours. After being cooled, the mixture was concentrated under reduced pressure, and the residue was partitioned between dichloromethane (150 mL) and water (150 mL). The aqueous layer was extracted with dichloromethane (2×150 mL), and the combined extracts were dried (MgSO4) and concentrated under reduced pressure. Purification by flash chromatography, eluting with hexane:ethyl acetate (9:1), then (3:1) and finally hexane:dichloromethane (1:1) gave methyl 2-amino-5,6-dimethyl-3-nitrobenzoate (12.94 g, 96%) as an orange solid.

Provenance & Evidence