Toluene → 4-hydroxy-1-phenyl-3-(2-phenylbutyryl)-1,8-naphthyridin-2(1H)-one

HRID 217380Notes

Reaction equation

HRID 217380 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)C(C3C=CC=CC=3)CC)=[CH:9][C:8]2=[O:29])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:30](N(CC)CC)[CH3:31].[C-]#N.[K+].C1[O:57][CH2:56][CH2:55]OCCOCCOCCOCCOC1.[C:58]1(C)[CH:63]=[CH:62][CH:61]=[CH:60][CH:59]=1>C(Cl)(Cl)Cl>[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:29])[C:9]=1[C:56](=[O:57])[CH:55]([C:58]1[CH:59]=[CH:60][CH:61]=[CH:62][CH:63]=1)[CH2:30][CH3:31]

Participants

7

Reactant 5

HCID 1140TolueneHCID 8471TriethylamineHCID 9032Potassium CyanideHCID 2855718-Crown-6HCID 689486761-phenyl-4-(2-phenylbutyryloxy)-1,8-naphthyridin-2(1H)-one

Product 1

HCID 689479984-hydroxy-1-phenyl-3-(2-phenylbutyryl)-1,8-naphthyridin-2(1H)-one

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Dry toluene (40 mL) was added to 1-phenyl-4-(2-phenylbutyryloxy)-1,8-naphthyridin-2(1H)-one (1.54 g, 4.0 mmol), triethylamine (407 mg, 4.0 mmol, 1 eq.), potassium cyanide (528 mg, 8.1 mmol, 2 eq.), and 18-crown-6 (211 mg), and the mixture was stirred at a room temperature overnight. Chloroform was added thereto. The insoluble residue was removed by using Celite, and the solvent of the resulting filtrate was distilled off. The resulting residue was purified by a flash column chromatography to give 4-hydroxy-1-phenyl-3-(2-phenylbutyryl)-1,8-naphthyridin-2(1H)-one as a form of crystal (123 mg, yield 8%).

Workup

  1. customThe insoluble residue was removed
  2. distillationthe solvent of the resulting filtrate was distilled off
  3. customThe resulting residue was purified by a flash column chromatography

Sources & evidence

ORD record
ord-ebc4cc4d3f104727a49fa10c274cc224
Source dataset
uspto-grants-2012_06
Patent number
US08193356B2

Reaction notes

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