2-Methyl-6-nitrobenzoic anhydride → HCID 86639714, compound

Participants

Reaction Steps

To a solution of MNBA (54 mg, 0.16 mmol) and DMAP (38 mg, 0.31 mmol) in CH2Cl2 (29 mL) was added dropwise a solution of the acid 5A (137 mg, 0.13 mmol) in CH2Cl2 (117 mL) over 4.5 h, this was then stirred overnight at room temperature. The reaction mixture was washed sequentially with HCl (1M, 40 mL), sodium hydrogen carbonate (40 ml) and sat. brine (40 mL) before being dried (MgSO4), filtered and concentrated in vacuo to give a brown solid. Purification by column chromatography on silica gel (eluent 4:6-1:1 EtOAc/Hexane increased to 1:9 MeOH/CHCl3) gave 6A (79.4 mg, 0.08 mmol, 58%) as a white/brown solid: Rf 0.14 EtOAc/Hexane (4:6).

Provenance & Evidence