Hydrazine hydrate (1:1) → HCID 178514874, compound

HRID 217400Notes

Reaction equation

HRID 217400 reaction equation
O[C:2]1[C:11]2[C:6](=[CH:7][N: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])[C:3]=1[C:19](=O)[CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.O.[NH2:29][NH2:30].C(=O)([O-])O.[Na+]>CN(C=O)C>[CH2:20]([C:19]1[C:3]2[C:4](=[O:18])[N:5]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[C:6]3[CH:7]=[N:8][CH:9]=[CH:10][C:11]=3[C:2]=2[NH:30][N:29]=1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

5

Reactant 3

HCID 24654Hydrazine hydrate (1:1)HCID 516892Sodium BicarbonateHCID 68950406HCID 68950406, compound

Product 1

HCID 178514874HCID 178514874, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
105 °C

Procedure

To a suspension of 4-hydroxy-1-phenyl-3-phenylacetyl-1,7-naphthyridin-2(1H)-one (100 mg, 0.28 mmol) produced in Synthesis Example 26 in DMF (3 mL) was added hydrazine monohydrate (purity of 80%, 68 μL), and the mixture was stirred at 100 to 110° C. for 2 hours. To the reaction solution was added a sodium hydrogencarbonate aqueous solution. The resulting precipitate was separated by filtration, recrystallized from ethanol, and dried to give 3-benzyl-5-phenyl-1H-pyrazolo[4,3-c][1,7]naphthyridin-4(5H)-one (78 mg, 79%).

Workup

  1. customThe resulting precipitate was separated by filtration
  2. customrecrystallized from ethanol
  3. customdried

Sources & evidence

ORD record
ord-23a30355241740729245f946e223af6d
Source dataset
uspto-grants-2012_06
Patent number
US08193356B2

Reaction notes

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