HCID 22105408, compound → HCID 22105402, compound

HRID 1455894Notes

Reaction equation

HRID 1455894 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH:3]=[C:2]1[C:10]([NH:12][C:13]1[CH:14]=[C:15]2[C:19](=[CH:20][CH:21]=1)[NH:18][C:17]([CH2:22][OH:23])=[CH:16]2)=[O:11]>C(O)C.O=[Mn]=O>[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH:3]=[C:2]1[C:10]([NH:12][C:13]1[CH:14]=[C:15]2[C:19](=[CH:20][CH:21]=1)[NH:18][C:17]([CH:22]=[O:23])=[CH:16]2)=[O:11]

Participants

4

Reactant 1

HCID 22105408HCID 22105408, compound

Product 1

HCID 22105402HCID 22105402, compoundYield 54%

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 702EthanolSolvent

Procedure

To a solution of 20(100 mg, 0.33 mmol) in ethanol (15 mL) was added MnO2 (0.5 g) and the reaction mixture was stirred for 4 h at room temperature. The reaction mixture was filtered through celite and the solid was washed with ethanol. Solvent was removed in vacuo and a grey solid 21 was obtained (54 mg, 54% yield). An analytical sample was recrystallized in ethyl acetate. mp: 253° C. (dec). 1H NMR (DMSO-d6, ppm): 10.60 (brs, 1 H, NH), 9.85, (s, 1 H, NH), 8.26 (s, 1 H, CHO), 7.84-7.35 (m, 9 H, Ar--H). Anal. (C18H12N2O3 0.3H2O), C, H, N.

Workup

  1. filtrationThe reaction mixture was filtered through celite
  2. washthe solid was washed with ethanol
  3. customSolvent was removed in vacuo

Sources & evidence

ORD record
ord-df39de823607452ca5e63e4b8aa1d301
Source dataset
uspto-grants-1998_12
Patent number
US05843937

Reaction notes

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