Sodium hydride → HCID 68951216, compound

HRID 217375

Reaction equation

HRID 217375 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]=[C:14]([O:18][C:19]([F:22])([F:21])[F:20])[CH:13]=2)[C:4](=[O:23])[CH:3]=1.[H-].[Na+].[H][H].[C:28]1([CH:34]([CH3:38])[C:35](Cl)=[O:36])[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.C(=O)([O-])O.[Na+]>CN(C=O)C>[C:28]1([CH:34]([CH3:38])[C:35]([O:1][C:2]2[C:11]3[C:6](=[N:7][CH:8]=[CH:9][CH:10]=3)[N:5]([C:12]3[CH:17]=[CH:16][CH:15]=[C:14]([O:18][C:19]([F:22])([F:20])[F:21])[CH:13]=3)[C:4](=[O:23])[CH:3]=2)=[O:36])[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Participants

7

Reactant 5

HCID 24758Sodium hydrideHCID 516892Sodium BicarbonateHCID 2760403Hydratropoyl chlorideHCID 689472714-hydroxy-1-(3-trifluoromethoxyphenyl)-1,8-naphthyridin-2(1H)-oneHCID 178418361HCID 178418361, compound

Product 1

HCID 68951216HCID 68951216, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In accordance with a process described in JP-61-246183A, 4-hydroxy-1-(3-trifluoromethoxyphenyl)-1,8-naphthyridin-2(1H)-one was synthesized. To a suspension of the synthesized compound (967 mg, 3.0 mmol) in DMF (24 mL) was added sodium hydride (purity of about 60%, 120 mg, 1.0 eq.). The mixture was stirred until no more hydrogen was generated, to obtain a solution. Then, 2-phenylpropionyl chloride (1.2 eq.) was added thereto, and the mixture was stirred at a room temperature for 1 hour. To the mixture was added a saturated sodium hydrogencarbonate aqueous solution, and the resulting precipitate was separated by filtration, washed with water, and dried to give 4-(2-phenylpropionyloxy)-1-(3-trifluoromethoxyphenyl)-1,8-naphthyridin-2(1H)-one as a form of crystal (1.14 g, yield 84%).

Workup

  1. customwas synthesized
  2. customto obtain a solution
  3. customthe resulting precipitate was separated by filtration
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-7184c74a6fd446eebef6ee7c63ab62c3
Source dataset
uspto-grants-2012_06
Patent number
US08193356B2

Linked notes

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