Dimethylformamide → HCID 59591088, compound

Participants

Reaction Steps

To a solution of 1,1-dimethylethyl 6-[(hydroxyamino)(imino)methyl]-5-methyl-1-(4-oxoheptyl)-3,4-dihydro-2(1H)-isoquinolinecarboxylate (Preparation 27; 230 mg, 0.551 mmol) in N,N-Dimethylformamide (DMF) (5 ml) was added triethylamine (0.115 ml, 0.826 mmol) followed by 3-chloro-4-[(1-methylethyl)oxy]benzoyl chloride (Preparation 33; 154 mg, 0.661 mmol) in DMF (2 ml) dropwise over one minute at room temperature under nitrogen. The resulting mixture was stirred for 1 h at room temperature, then heated at 120° C. for ca. 2.5 h. Most of the solvent was removed and the residue dissolved in ethyl acetate. The solution was washed with saturated aqueous sodium bicarbonate then brine, dried over MgSO4 and concentrated in vacuo to give the crude product (ca. 350 mg). Purification by flash chromatography on silica gel, eluting with 5-25% ethyl acetate in cyclohexane gave the title compound (110 mg) as a colourless oil.

Provenance & Evidence