Hydrochloric Acid → HCID 178514871, compound

HRID 1822247Notes

Reaction equation

HRID 1822247 reaction equation
O[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]([N+:18]([O-:20])=[O:19])[CH:13]=2)[C:4](=[O:21])[CH:3]=1.[H-].[Na+].[H][H].[C:26]1([CH2:32][C:33](Cl)=O)[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.Cl.O.[NH2:38][NH2:39]>CN(C=O)C.O>[CH2:32]([C:33]1[C:3]2[C:4](=[O:21])[N:5]([C:12]3[CH:17]=[CH:16][CH:15]=[C:14]([N+:18]([O-:20])=[O:19])[CH:13]=3)[C:6]3[N:7]=[CH:8][CH:9]=[CH:10][C:11]=3[C:2]=2[NH:39][N:38]=1)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

9

Reactant 6

HCID 313Hydrochloric AcidHCID 7679Phenylacetyl chlorideHCID 24654Hydrazine hydrate (1:1)HCID 24758Sodium hydrideHCID 546762034-hydroxy-1-(3-nitrophenyl)-1,8-naphthyridin-2(1H)-oneHCID 178418361HCID 178418361, compound

Product 1

HCID 178514871HCID 178514871, compoundYield 45%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6228DimethylformamideSolvent

Procedure

To a suspension of 4-hydroxy-1-(3-nitrophenyl)-1,8-naphthyridin-2 (1H)-one (1.13 g, 4 mmol, obtained in Synthetic Example 4 (3)) in DMF (16 ml) was added sodium hydride (about 60%, 384 mg, 9.6 mmol, 2.4 eq.), and the mixture was stirred until the production of hydrogen was completed. Next, after phenylacetyl chloride (742 mg, 4.8 mmol, 1.2 eq.) was added, the mixture was stirred at room temperature, followed by addition of water. After acidified with hydrochloric acid, it was filtered to give precipitates which were washed with water and suspended in DMF (16 mL) without further purification. To the suspension was added hydrazine monohydrate (80%, 448 μl, 11.2 mmol, 2.8 eq.), and the resultant mixture was stirred at 100 to 110° C. overnight. The reaction mixture was admixed with water, and filtered to give precipitates which were dried to afford 3-benzyl-5-(3-nitrophenyl)-1H-pyrazolo[4,3-c][1,8]naphthyridin-4 (5H)-one (714 mg, 45%).

Workup

  1. filtrationwas filtered
  2. customto give
  3. customprecipitates which
  4. washwere washed with water
  5. customsuspended in DMF (16 mL) without further purification
  6. filtrationfiltered
  7. customto give
  8. customprecipitates which
  9. customwere dried

Sources & evidence

ORD record
ord-dd76ceab9c9b4f309cf4aaeb27e1b2b2
Source dataset
uspto-grants-2009_10
Patent number
US07608716B2

Reaction notes

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