Hydrazine hydrate (1:1) → HCID 19380142, compound

HRID 2254026Notes

Reaction equation

HRID 2254026 reaction equation
[C:1]1([C:7]2[CH:19]=[C:10]3[CH:11]=[CH:12][C:13]4[C:18]([N:9]3[N:8]=2)=[CH:17][CH:16]=[CH:15][CH:14]=4)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.O.[NH2:21]N>[Pd].C(O)C>[NH2:21][C:19]1[C:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)=[N:8][N:9]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH:12]=[CH:11][C:10]=12

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 134447Pyrazolo(1,5-a)quinoline, 2-phenyl-

Product 1

HCID 19380142HCID 19380142, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

1.0 g. 2-Phenylpyrazolo[1,5-a]quinoline (see J. Het. Chem., 12, 481/1975) are nitrosated analogously to Example 3. There is obtained 1 g. (89% of theory) of the corresponding 3-nitroso compound which is suspended in 90 ml. ethanol and mixed with 200 mg. palladium on carbon. The mixture is heated to 80° C. and 0.25 ml. hydrazine hydrate added portionwise thereto. After 10 minutes, the palladium-carbon is filtered off and the filtrate is evaporated. The residue is dissolved in ethanol and mixed with ethanolic hydrogen chloride. The precipitated hydrochloride is filtered off with suction to give 0.7 g. (72% of theory) of the title compound; m.p. 255°-258° C. TLC (Silica gel/methylene chloride): Rf =0.2

Workup

  1. customThere is obtained 1 g
  2. filtrationthe palladium-carbon is filtered off
  3. customthe filtrate is evaporated
  4. dissolutionThe residue is dissolved in ethanol
  5. additionmixed with ethanolic hydrogen chloride
  6. filtrationThe precipitated hydrochloride is filtered off with suction
  7. customto give 0.7 g

Sources & evidence

ORD record
ord-838a547f5358453593cb388b74140595
Source dataset
uspto-grants-1993_08
Patent number
US05234818

Reaction notes

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