Water → HCID 178419467, compound

HRID 1614167Notes

Reaction equation

HRID 1614167 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 hydrate (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 NaHCO 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-f7725d41b44846c2b010858af37be6ff
Source dataset
uspto-grants-1993_03
Patent number
US05196421

Reaction notes

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