Oxalic Acid → HCID 10826192, compound

HRID 2289493Notes

Reaction equation

HRID 2289493 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[C:21]3[C:20]4[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=4)[NH:14][C:13]=3[CH2:12][NH:11][CH2:10]2)=[CH:5][CH:4]=1.C(O)(=O)C(O)=O>CC(O)=O>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([C:9]2[C:21]3[C:20]4[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=4)[NH:14][C:13]=3[CH:12]=[N:11][CH:10]=2)=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 971Oxalic AcidHCID 10802567HCID 10802567, compound

Product 1

HCID 10826192HCID 10826192, compoundYield 63.1%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

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.

Workup

  1. waitThe resulting mixture was kept at rt for 1 h
  2. filtrationThe yellow solid was filtered
  3. washthe filtered cake was washed with MeOH
  4. additionThe pH of the aqueous phase was adjusted to 7 by the addition of solid NaHCO3
  5. customThe phases were separated
  6. extractionthe aqueous phase was extracted 10×, 40 mL each
  7. washThe combined CH2Cl2 extracts were washed with 5% aqueous NaHCO3
  8. dry with materialdried (MgSO4)
  9. concentrationconcentrated to ~30 mL

Sources & evidence

ORD record
ord-a15b3bdebbf04eecbba8240bfc4fac11
Source dataset
uspto-grants-2000_07
Patent number
US06093723

Reaction notes

Loading…