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

HRID 217378Notes

Reaction equation

HRID 217378 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]([C:27]([F:30])([F:29])[F:28])[CH:22]=3)[C:13](=[O:31])[CH:12]=2)=O)C=CC=CC=1.[CH2:33](N(CC)CC)C.[C-]#N.[K+].C1[O:60][CH2:59][CH2:58]OCCOCCOCCOCCOC1.[C:61]1(C)[CH:66]=[CH:65][CH:64]=[CH:63][CH:62]=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]([C:27]([F:29])([F:30])[F:28])[CH:22]=2)[C:13](=[O:31])[C:12]=1[C:59](=[O:60])[CH:58]([C:61]1[CH:66]=[CH:65][CH:64]=[CH:63][CH:62]=1)[CH3:33]

Participants

7

Reactant 5

HCID 1140TolueneHCID 8471TriethylamineHCID 9032Potassium CyanideHCID 2855718-Crown-6HCID 689453654-(2-phenylpropionyloxy)-1-(3-trifluoromethylphenyl)-1,8-naphthyridin-2(1H)-one

Product 1

HCID 689460604-hydroxy-3-(2-phenylpropionyl)-1-(3-trifluoromethylphenyl)-1,8-naphthyridin-2(1H)-one

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Dry toluene (20 mL) was added to 4-(2-phenylpropionyloxy)-1-(3-trifluoromethylphenyl)-1,8-naphthyridin-2(1H)-one (890 mg, 2.0 mmol), triethylamine (209 mg, 2.1 mmol, 1 eq.), potassium cyanide (266 mg, 4.1 mmol, 2 eq.), and 18-crown-6 (107 mg), and the mixture was stirred at a room temperature for 7.5 hours. 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-trifluoromethylphenyl)-1,8-naphthyridin-2(1H)-one as a form of crystal (150 mg, yield 17%).

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-4f7e97e558bf4c41874ce6b3bd9ecce2
Source dataset
uspto-grants-2012_06
Patent number
US08193356B2

Reaction notes

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