Toluene → HCID 54676186, compound

HRID 1822193Notes

Reaction equation

HRID 1822193 reaction equation
[C:1]1([N:7]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][N:15]=3)[C:10]([O:17]C(=O)CC3C=CC=CC=3)=[CH:9][C:8]2=[O:27])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N(CC)CC)C.[C-]#N.[K+].C1[O:55][CH2:54][CH2:53]OCCOCCOCCOCCOC1.C(=O)([O-])O.[Na+].[C:61]1(C)[CH:66]=[CH:65][CH:64]=[CH:63][CH:62]=1>ClCCl>[OH:17][C:10]1[C:11]2[C:16](=[N:15][CH:14]=[CH:13][CH:12]=2)[N:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[C:8](=[O:27])[C:9]=1[C:54](=[O:55])[CH2:53][C:61]1[CH:66]=[CH:65][CH:64]=[CH:63][CH:62]=1

Participants

8

Reactant 6

HCID 1140TolueneHCID 8471TriethylamineHCID 9032Potassium CyanideHCID 2855718-Crown-6HCID 516892Sodium BicarbonateHCID 67397308HCID 67397308, compound

Product 1

HCID 54676186HCID 54676186, compoundYield 44%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of 1-phenyl-4-phenylacetoxy-1,8-naphthyridin-2 (1H)-one (1.34 g, 3.7 mmol), triethylamine (379 mg, 3.7 mmol), potassium cyanide (491 mg, 7.5 mmol), and 18-crown-6 (197 mg) was added dry toluene (35 ml), and the mixture was stirred at room temperature overnight, admixed with saturated aqueous sodium hydrogen carbonate and dichloromethane. The organic layer was washed with saturated aqueous sodium hydrogen carbonate, and successively with saturated aqueous sodium chloride. The organic layer was collected, dried over anhydrous magnesium sulfate, and evaporated. The resulting residue was purified by flash column chromatography to afford 4-hydroxy-3-(1-oxo-2-phenylethyl)-1-phenyl-1,8-naphthyridin-2 (1H)-one (583 mg, 44%) as crystals.

Workup

  1. washThe organic layer was washed with saturated aqueous sodium hydrogen carbonate
  2. customThe organic layer was collected
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customevaporated
  5. customThe resulting residue was purified by flash column chromatography

Sources & evidence

ORD record
ord-0e02c19af5514d298327aed62847bcbc
Source dataset
uspto-grants-2009_10
Patent number
US07608716B2

Reaction notes

Loading…