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Sodium hydride → 4-hydroxy-1-phenyl-3-(2-trifluoromethylphenylacetyl)-1,8-naphthyridin-2(1H)-one

HRID 217366
Notes
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Reaction equation

HRID 217366 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:34])([F:33])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[CH2:29][C:30](Cl)=[O:31]>CN(C=O)C>[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:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:4](=[O:18])[C:3]=1[C:30](=[O:31])[CH2:29][C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=1[C:22]([F:33])([F:21])[F:34]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 132018232-(Trifluoromethyl)phenylacetyl chlorideHCID 546864734-Hydroxy-1-phenyl-1,8-naphthyridin-2(1H)-one

Product 1

HCID 689497164-hydroxy-1-phenyl-3-(2-trifluoromethylphenylacetyl)-1,8-naphthyridin-2(1H)-one

Reagents, catalysts & solvents 1

HCID 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%, 352 mg, 8.8 mmol, 2.2 eq.), and the mixture was stirred at a room temperature for 45 minutes. Then, 2-trifluoromethylphenylacetyl chloride (4.8 mmol, 1.2 eq.) was added thereto with cooling in an ice bath, and the mixture was stirred at a room temperature for 1.5 hours. Thereafter, the resulting mixture was purified by a flash column chromatography to give 4-hydroxy-1-phenyl-3-(2-trifluoromethylphenylacetyl)-1,8-naphthyridin-2(1H)-one as a form of crystal (972 mg, yield 57%).

Workup

  1. customwas synthesized
  2. temperaturewith cooling in an ice bath
  3. stirringthe mixture was stirred at a room temperature for 1.5 hours
  4. customThereafter, the resulting mixture was purified by a flash column chromatography

Sources & evidence

ORD record
ord-13ab0c9a28754f2a8cc6aa523b42158a
Source dataset
uspto-grants-2012_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08193356B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes