Sodium hydride → 1-phenyl-4-(4,4,4-trifluorobutyryloxy)-1,8-naphthyridin-2(1H)-one

HRID 217374Notes

Reaction equation

HRID 217374 reaction equation
[OH:1][C:2]1[C:11]2[C:6](=[N:7][CH:8]=[CH:9][CH:10]=2)[N:5]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:4](=[O:18])[CH:3]=1.[H-].[Na+].[F:21][C:22]([F:29])([F:28])[CH2:23][CH2:24][C:25](Cl)=[O:26].C(=O)([O-])O.[Na+]>CN(C=O)C.O>[C:12]1([N:5]2[C:6]3[C:11](=[CH:10][CH:9]=[CH:8][N:7]=3)[C:2]([O:1][C:25](=[O:26])[CH2:24][CH2:23][C:22]([F:29])([F:28])[F:21])=[CH:3][C:4]2=[O:18])[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

7

Reactant 4

HCID 24758Sodium hydrideHCID 516892Sodium BicarbonateHCID 151044744,4,4-Trifluorobutanoyl chlorideHCID 546864734-Hydroxy-1-phenyl-1,8-naphthyridin-2(1H)-one

Product 1

HCID 689498031-phenyl-4-(4,4,4-trifluorobutyryloxy)-1,8-naphthyridin-2(1H)-one

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

In accordance with a process described in JP-61-246183A, 4-hydroxy-1-phenyl-1,8-naphthyridin-2(1H)-one was synthesized. To a suspension of the synthesized compound (953 mg, 4.0 mmol) in DMF (32 mL) was added sodium hydride (purity of about 60%, 176 mg, 4.4 mmol, 1.1 eq.), and the mixture was stirred at a room temperature for 40 minutes. Then, 4,4,4-trifluorobutyryl chloride (4.4 mmol, 1.1 eq.) was added thereto with cooling in an ice bath, and the mixture was stirred at a room temperature for 2 hours. Thereafter, a sodium hydrogencarbonate aqueous solution and water were added to the reaction solution, and the precipitate was separated by filtration and dried to give 1-phenyl-4-(4,4,4-trifluorobutyryloxy)-1,8-naphthyridin-2(1H)-one as a form of crystal (955 mg, yield 66%).

Workup

  1. customwas synthesized
  2. temperaturewith cooling in an ice bath
  3. stirringthe mixture was stirred at a room temperature for 2 hours
  4. customthe precipitate was separated by filtration
  5. customdried

Sources & evidence

ORD record
ord-0a39c5683a7645b4ae72e4d2c5fe2e91
Source dataset
uspto-grants-2012_06
Patent number
US08193356B2

Reaction notes

Loading…