Triethylamine → 3-cyclohexylacetyl-4-hydroxy-1-phenyl-1,8-naphthyridin-2(1H)-one

HRID 217373Notes

Reaction equation

HRID 217373 reaction equation
C1(CC([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]=[CH:23][CH:22]=3)[C:13](=[O:27])[CH:12]=2)=O)CCCCC1.C(N([CH2:33][CH3:34])CC)C.[C-]#N.[K+].C1[O:55][CH2:54][CH2:53]OCCOCCOCCOCCOC1>ClCCl.C1(C)C=CC=CC=1>[CH:34]1([CH2:53][C:54]([C:12]2[C:13](=[O:27])[N:14]([C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=3)[C:15]3[C:20]([C:11]=2[OH:10])=[CH:19][CH:18]=[CH:17][N:16]=3)=[O:55])[CH2:33][CH2:13][CH2:12][CH2:11][CH2:20]1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 9032Potassium CyanideHCID 2855718-Crown-6HCID 689460384-cyclohexylacetoxy-1-phenyl-1,8-naphthyridin-2(1H)-one

Product 1

HCID 689479453-cyclohexylacetyl-4-hydroxy-1-phenyl-1,8-naphthyridin-2(1H)-one

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Procedure

Dry toluene (30 mL) was added to 4-cyclohexylacetoxy-1-phenyl-1,8-naphthyridin-2(1H)-one (1.31 g, 3.61 mmol), triethylamine (0.50 mL, 3.61 mmol, 1 eq.), potassium cyanide (472 mg, 7.24 mmol, 2 eq.), and 18-crown-6 (190 mg), and the mixtures was stirred at a room temperature for 2 days. Dichloromethane was added thereto. The mixture was filtered by using Celite, and then the solvent was distilled off. The resulting residue was purified by a flash column chromatography to give an objective 3-cyclohexylacetyl-4-hydroxy-1-phenyl-1,8-naphthyridin-2(1H)-one as a form of crystal (625 mg, yield 48%).

Workup

  1. filtrationThe mixture was filtered
  2. distillationthe solvent was distilled off
  3. customThe resulting residue was purified by a flash column chromatography

Sources & evidence

ORD record
ord-bd55b59b66ae44afbab599f8b48bef3b
Source dataset
uspto-grants-2012_06
Patent number
US08193356B2

Reaction notes

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