Bis(2-pyridyl) ketone → HCID 406382, compound

HRID 1600880Notes

Reaction equation

HRID 1600880 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][C:2]1=[O:10].[N:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[C:17]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=1)=O.C([O-])(=O)C.[NH4+]>C(O)(=O)C>[N:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[C:17]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=1)=[C:3]1[C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[NH:1][C:2]1=[O:10]

Participants

5

Reactant 3

HCID 88065Bis(2-pyridyl) ketoneHCID 321710OxindoleHCID 517165Ammonium Acetate

Product 1

HCID 406382HCID 406382, compoundYield 78.8%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
100 °C

Procedure

To 50 ml of acetic acid were poured 4.2 g of 97% oxindole, 5.0 g of di-2-pyridylketone, and 20.9 g of ammonium acetate. The mixture was heated for 12 hours at 100° C. Thereafter, the solvent was evaporated, and the residue was extracted with ethyl acetate. The extract was washed with water, saturated sodium bicarbonate water, and saturated brine, and subsequently dried over sodium sulfate. The resultant crude product was purified by silica gel column chromatography (ethyl acetate), to thereby obtain 6.4 g (yield 78.8%) of the title compound in the form of yellow crystals. The melting point and elementary analysis data are shown in Table 17, and NMR and MS spectrum data are shown in Table 18.

Workup

  1. customThereafter, the solvent was evaporated
  2. extractionthe residue was extracted with ethyl acetate
  3. washThe extract was washed with water, saturated sodium bicarbonate water, and saturated brine
  4. dry with materialsubsequently dried over sodium sulfate
  5. customThe resultant crude product was purified by silica gel column chromatography (ethyl acetate)

Sources & evidence

ORD record
ord-3acfdb750fa44fff8eddc1e8106b0418
Source dataset
uspto-grants-1999_11
Patent number
US05977130

Reaction notes

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