Diethyl Oxalate → Ethyl (1-acetyl-6-nitro-4-oxo-1,2,3,4-tetrahydroquinolin-3-yl)(oxo)acetate

Participants

Reaction Steps

To the material of Step 2 (4.8 g, 0.0205 mol) in THF (25 mL) at −78° C., was added the lithium bis(trimethylsilyl)amide (20.5 mL of a 1M in THF solution). The diethyl oxalate (3 g, d=1.076 g/mL, 2.8 mL, 0.0205 mol) was then added and the reaction mixture was allowed to warm to room temperature and stir overnight. The slurry was then filtered to give an orange solid. 6.1 g (MW=334.28 g/mol, 90% yield). LC/MS m/z=335 (m+1).

Provenance & Evidence