2-Methyl-6-nitrobenzoic anhydride → HCID 86639720, compound

Participants

Reaction Steps

To a solution of 2-methyl-6-nitrobenzoic anhydride (MNBA) (32.7 mg, 0.095 mmol) and DMAP (22.5 mg, 0.184 mmol) in CH2Cl2 (20 mL) was added dropwise a solution of acid 5C (76 mg, 0.075 mmol) in CH2Cl2/THF (2:1, 66 mL) over 3 hours. After a further 12 h the reaction was quenched by the addition of 1M HCl (30 mL). The organic phase was separated (extracting with CH2Cl2) and washed with sat NaHCO3 (30 mL), followed by brine (30 mL). The combined organic phase was dried (MgSO4), filtered and concentrated in vacuo to give a yellow oil. Purification by column chromatography on silica gel (eluent 40% EtOAc/Hexane) gave 6C (35 mg, 0.035 mmol, 47%) as a yellow oil.

Provenance & Evidence