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

HRID 217370Notes

Reaction equation

HRID 217370 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)C)=[CH:9][C:8]2=[O:28])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:29](N(CC)CC)C.[C-]#N.[K+].C1[O:56][CH2:55][CH2:54]OCCOCCOCCOCCOC1.[C:57]1(C)[CH:62]=[CH:61][CH:60]=[CH:59][CH:58]=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:28])[C:9]=1[C:55](=[O:56])[CH:54]([C:57]1[CH:62]=[CH:61][CH:60]=[CH:59][CH:58]=1)[CH3:29]

Participants

7

Reactant 5

HCID 1140TolueneHCID 8471TriethylamineHCID 9032Potassium CyanideHCID 2855718-Crown-6HCID 689479261-phenyl-4-(2-phenylpropionyloxy)-1,8-naphthyridin-2(1H)-one

Product 1

HCID 689498344-hydroxy-1-phenyl-3-(2-phenylpropionyl)-1,8-naphthyridin-2(1H)-one

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Dry toluene (50 mL) was added to 1-Phenyl-4-(2-phenylpropionyloxy)-1,8-naphthyridin-2(1H)-one (2.0 g, 5.40 mmol), triethylamine (546 mg, 5.40 mmol, 1 eq.), and potassium cyanide (706 mg, 10.8 mmol, 2 eq.), 18-crown-6 (280 mg), and the mixture was stirred at a room temperature for 3 days. 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-phenylpropionyl)-1,8-naphthyridin-2(1H)-one as a form of crystal (714 mg, yield 36%).

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-adbe0ff8cbac46189918660f03af0f3c
Source dataset
uspto-grants-2012_06
Patent number
US08193356B2

Reaction notes

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