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

HRID 217376Notes

Reaction equation

HRID 217376 reaction equation
C1(C(C)C([O:10][C:11]2[C:20]3[C:15](=[N:16][CH:17]=[CH:18][CH:19]=3)[N:14]([C:21]3[CH:26]=[CH:25][CH:24]=[C:23]([O:27][C:28]([F:31])([F:30])[F:29])[CH:22]=3)[C:13](=[O:32])[CH:12]=2)=O)C=CC=CC=1.[CH2:34](N(CC)CC)C.[C-]#N.[K+].C1[O:61][CH2:60][CH2:59]OCCOCCOCCOCCOC1.[C:62]1(C)[CH:67]=[CH:66][CH:65]=[CH:64][CH:63]=1>C(Cl)(Cl)Cl>[OH:10][C:11]1[C:20]2[C:15](=[N:16][CH:17]=[CH:18][CH:19]=2)[N:14]([C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([O:27][C:28]([F:29])([F:31])[F:30])[CH:22]=2)[C:13](=[O:32])[C:12]=1[C:60](=[O:61])[CH:59]([C:62]1[CH:67]=[CH:66][CH:65]=[CH:64][CH:63]=1)[CH3:34]

Participants

7

Reactant 5

HCID 1140TolueneHCID 8471TriethylamineHCID 9032Potassium CyanideHCID 2855718-Crown-6HCID 689512164-(2-phenylpropionyloxy)-1-(3-trifluoromethoxyphenyl)-1,8-naphthyridin-2(1H)-one

Product 1

HCID 689489354-hydroxy-3-(2-phenylpropionyl)-1-(3-trifluoromethoxyphenyl)-1,8-naphthyridin-2(1H)-one

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Dry toluene (24 mL) was added to 4-(2-phenylpropionyloxy)-1-(3-trifluoromethoxyphenyl)-1,8-naphthyridin-2(1H)-one (1.1 g, 2.4 mmol), triethylamine (249 mg, 2.5 mmol, 1 eq.), potassium cyanide (316 mg, 4.9 mmol, 2 eq.), and 18-crown-6 (128 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-3-(2-phenylpropionyl)-1-(3-trifluoromethoxyphenyl)-1,8-naphthyridin-2(1H)-one as a form of crystal (310 mg, yield 28%).

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-753e50f6b3bc4ea287f20fa0d2d55208
Source dataset
uspto-grants-2012_06
Patent number
US08193356B2

Reaction notes

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