Water → HCID 178419467, compound

HRID 465335Notes

Reaction equation

HRID 465335 reaction equation
[Br:1][C:2]1[C:3](O)=[N:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2.O.[NH2:14][NH2:15].Cl.Cl.NN.O>C(O)CO>[Br:1][C:2]1[C:3]([NH:4][C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=2)=[N:14][NH:15][CH:11]=1

Participants

6

Reactant 4

HCID 962WaterHCID 17548Hydrazine, dihydrochlorideHCID 24654Hydrazine hydrate (1:1)HCID 178517115HCID 178517115, compound

Product 1

HCID 178419467HCID 178419467, compound

Reagents, catalysts & solvents 1

HCID 174Ethylene GlycolSolvent

Procedure

The bromohydroxyquinoline (1.97 g, 8.79 mmol) was dissolved in 21 ml of ethylene glycol and hydrazine hydrat (4.2 ml) was added. To this mixture were added 1.3 g (12.2 mmol) of hydrazine dihydrochloride, and the resulting mixture was heated to reflux and stirred under nitrogen. The resulting material was poured onto 300 ml of H2O. The mixture was extracted with CH2Cl2, basified with NaHCO3 and extracted further with CH2Cl2. The combined organic portions were washed with water, dried over Na2SO4, filtered, and concentrated in vacuo to give a brown oil, yielding bromoanilinopyrazole (i.e., 3-(2-amino-5-bromophenyl)pyrazole).

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureto reflux
  3. extractionThe mixture was extracted with CH2Cl2
  4. extractionextracted further with CH2Cl2
  5. washThe combined organic portions were washed with water
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customto give a brown oil

Sources & evidence

ORD record
ord-f214bc5bf69247e5a3a8f05209bf673b
Source dataset
uspto-grants-1992_10
Patent number
US05153196

Reaction notes

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