Hydrochloric Acid → HCID 54676179, compound

HRID 1822194Notes

Reaction equation

HRID 1822194 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([N:9]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][N:17]=3)[C:12]([OH:19])=[CH:11][C:10]2=[O:20])[CH:6]=[CH:7][CH:8]=1)#[N:2].[H-].[Na+].[H][H].[C:25]1([CH2:31][C:32](Cl)=[O:33])[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.Cl>CN(C=O)C.O>[C:1]([C:3]1[CH:4]=[C:5]([N:9]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][N:17]=3)[C:12]([OH:19])=[C:11]([C:32](=[O:33])[CH2:31][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[C:10]2=[O:20])[CH:6]=[CH:7][CH:8]=1)#[N:2]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 7679Phenylacetyl chlorideHCID 24758Sodium hydrideHCID 54676200HCID 54676200, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 54676179HCID 54676179, compoundYield 25%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a suspension of a mixture containing 1-(3-cyanophenyl)-4-hydroxy-1,8-naphthyridin-2 (1H)-one (958 mg, 3.64 mmol) in DMF (16 ml) was added sodium hydride (about 60%, 350 mg, 8.74 mmol, 2.4 eq.), and the mixture was stirred until the production of hydrogen was completed. Next, after phenylacetyl chloride (563 mg, 3.64 mmol, 1.0 eq.) was added, the mixture was stirred at room temperature, admixed with water, acidified with hydrochloric acid, filtered off to give precipitates which were washed with water. The resultant residue was purified by flash column chromatography to afford 1-(3-cyanophenyl)-4-hydroxy-3-(1-oxo-2-phenylethyl)-1,8-naphthyridin-2 (1H)-one (341 mg, 25%).

Workup

  1. additionTo a suspension of a mixture
  2. filtrationfiltered off
  3. customto give
  4. customprecipitates which
  5. washwere washed with water
  6. customThe resultant residue was purified by flash column chromatography

Sources & evidence

ORD record
ord-1b95f2cd5c024d11882c49b87b3c21a7
Source dataset
uspto-grants-2009_10
Patent number
US07608716B2

Reaction notes

Loading…