Phenylhydrazine → HCID 178515215, compound

HRID 1633247Notes

Reaction equation

HRID 1633247 reaction equation
O[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][N:10]=2)[N:5]=[CH:4][C:3]=1[C:12]([O:14]CC)=O.C(Cl)(=O)C(Cl)=O.C(N(C(C)C)CC)(C)C.[C:32]1([NH:38][NH2:39])[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1>CN(C)C=O.C(Cl)Cl.O>[C:32]1([N:38]2[C:12](=[O:14])[C:3]3=[CH:4][NH:5][C:6]4[CH:7]=[CH:8][CH:9]=[N:10][C:11]=4[C:2]3=[N:39]2)[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1

Participants

8

Reactant 4

HCID 7516PhenylhydrazineHCID 65578Oxalyl chlorideHCID 81531DiisopropylethylamineHCID 178469573HCID 178469573, compound

Product 1

HCID 178515215HCID 178515215, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a slurry of 1.5 g of ethyl 4-hydroxy-1,5-naphthyridine-3-carboxylate (prepared according to J. Inorg. Nucl. Chem., (1966) 28, 2439) in 17 ml of dimethylformamide is added 0.907 g of oxalyl chloride in 2 ml of methylene chloride while maintaining the reaction temperature between -25° and -30°. The mixture is stirred at -25° for 35 minutes. A solution of 0.995 g of diisopropylethylamine and 0.833 g of phenylhydrazine in 4 ml of methylene chloride is added to the mixture in 8 minutes at -30° to -25°. The mixture is then stirred for 30 minutes at -25°, 20 minutes at 0° and 40 minutes at 23°. The resultant dark purple solution is poured into 60 ml of water. Dark precipitate is collected, washed with water and crystallized from methanol to yield 2-phenyl-pyrazolo[4,3-c] [1,5]naphthyridin-3(5H)-one, m.p. 314°-316°.

Workup

  1. temperaturewhile maintaining the reaction temperature between -25° and -30°
  2. stirringThe mixture is then stirred for 30 minutes at -25°, 20 minutes at 0° and 40 minutes at 23°
  3. customDark precipitate is collected
  4. washwashed with water
  5. customcrystallized from methanol

Sources & evidence

ORD record
ord-4054b2332f69434db1d2e76cc3c223ea
Source dataset
uspto-grants-1984_10
Patent number
US04479955

Reaction notes

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