Oxalic Acid → HCID 10826192, compound

Participants

Reaction Steps

To a solution of 1.43 g (3.58 mmol) of 4-(p-methoxyphenyl)tetrahydro-β-carboline in 50 mL glacial AcOH was added 3.18 g (7.16 mmol) of Pb(OAc)4 with stirring at rt. After stiriing at rt for 40 min., 3.22 g (35.8 mmol) of oxalic acid was added. The resulting mixture was kept at rt for 1 h when yellow precipitate appeared. The yellow solid was filtered and the filtered cake was washed with MeOH. The solid product was suspended in 200 mL of H2O and 200 mL of CH2Cl2. The pH of the aqueous phase was adjusted to 7 by the addition of solid NaHCO3. The phases were separated and the aqueous phase was extracted 10×, 40 mL each, with CH2Cl2. The combined CH2Cl2 extracts were washed with 5% aqueous NaHCO3, dried (MgSO4) and concentrated to ~30 mL to precipitate out 0.62 g of product (63% yield), m.p. 235° C. (decomposed). Elemental Analysis Calcd for C18H14N2O: C,78.81; H,5.14; N,10.21. Found: C,78.68; H,5.27; N, 9.98.

Provenance & Evidence