Water → HCID 178422495, compound

HRID 638247Notes

Reaction equation

HRID 638247 reaction equation
Cl[C:2]1[C:11]2[C:6](=[N:7][C:8]([CH3:12])=[CH:9][CH:10]=2)[N:5]=[CH:4][C:3]=1[C:13]([O:15]CC)=[O:14].[C:18]1([NH:24][NH2:25])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.O>C(O)CCC.[OH-].[Na+]>[OH2:14].[CH3:12][C:8]1[CH:9]=[CH:10][C:11]2[C:2]3[C:3]([C:13](=[O:15])[N:24]([C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=4)[N:25]=3)=[CH:4][NH:5][C:6]=2[N:7]=1.[CH3:12][C:8]1[CH:9]=[CH:10][C:11]2[C:2]3[C:3]([C:13](=[O:15])[N:24]([C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=4)[N:25]=3)=[CH:4][NH:5][C:6]=2[N:7]=1

Participants

6

Reactant 3

HCID 962WaterHCID 7516PhenylhydrazineHCID 10562672Ethyl 4-chloro-7-methyl-1,8-naphthyridine-3-carboxylate

Product 1

HCID 178422495HCID 178422495, compound

Reagents, catalysts & solvents 2

HCID 2631-ButanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

A mixture of 3.0 g of ethyl 4-chloro-7-methyl-1,8-naphthyridine-3-carboxylate (prepared according to U.S. Pat. No. 3,786,043) and 1.42 g of phenylhydrazine in 30 ml of n-butanol is refluxed for 18 hours. The mixture is chilled in an ice bath and filtered to give a solid which is taken up in 50 ml of 1N sodium hydroxide and sufficient water to dissolve. The resulting solution is filtered to remove insoluble, washed with ether and neutralized with 3.0 g of ammonium chloride. The resulting mixture is filtered collecting a solid which is washed with water and dried to yield 7-methyl-2-phenylpyrazolo[4,3-c][1,8]naphthyridin-3(5H)-one hemihydrate, m.p. 305°-308°.

Workup

  1. customprepared
  2. temperatureThe mixture is chilled in an ice bath
  3. filtrationfiltered
  4. customto give a solid which
  5. filtrationThe resulting solution is filtered
  6. customto remove insoluble
  7. washwashed with ether and neutralized with 3.0 g of ammonium chloride
  8. filtrationThe resulting mixture is filtered
  9. customcollecting a solid which
  10. washis washed with water
  11. customdried

Sources & evidence

ORD record
ord-a37b97a6954f4f53ba31402a5fd4f02d
Source dataset
uspto-grants-1985_12
Patent number
US04560689

Reaction notes

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