Hydrochloric Acid → HCID 5875641, compound

HRID 1661539Notes

Reaction equation

HRID 1661539 reaction equation
[C:1]([C:4]1[CH:5]=[N:6][CH:7]=[CH:8][CH:9]=1)(=O)[CH3:2].Cl.[F:11][C:12]1[CH:17]=[CH:16][C:15]([NH:18][NH2:19])=[CH:14][CH:13]=1.Cl>C(O)C>[F:11][C:12]1[CH:17]=[CH:16][C:15]([NH:18]/[N:19]=[C:1](\[C:4]2[CH:5]=[N:6][CH:7]=[CH:8][CH:9]=2)/[CH3:2])=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 95893-AcetylpyridineHCID 699814-Fluorophenylhydrazine hydrochloride

Product 1

HCID 5875641HCID 5875641, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

3-Acetylpyridine (5.00 g, 40.45 mmol) and 4-fluorophenylhydrazine hydrochloride (6.44 g, 38.43 mmol) are suspended in ethanol (70 mL) and heated to reflux. After 1 h, HCl (4M in dioxane, 150 mL, 600 mmol) is added and the mixture is heated to reflux for 16 h. The mixture is concentrated in vacuo and taken up in a little ethanol. The solid is filtered off and washed with ethanol to give a yellow solid. The filtrate is concentrated to dryness. The resulting solid is washed with small amounts of ice-cold ethanol and filtered off. The two fractions are combined and used in the next step without further purification.

Workup

  1. temperatureheated to reflux
  2. temperaturethe mixture is heated
  3. temperatureto reflux for 16 h
  4. concentrationThe mixture is concentrated in vacuo
  5. filtrationThe solid is filtered off
  6. washwashed with ethanol
  7. customto give a yellow solid
  8. concentrationThe filtrate is concentrated to dryness
  9. washThe resulting solid is washed with small amounts of ice-cold ethanol
  10. filtrationfiltered off
  11. customused in the next step without further purification

Sources & evidence

ORD record
ord-ab51bd5001d941ce97be2b2c8e36e980
Source dataset
uspto-grants-2011_10
Patent number
US08030334B2

Reaction notes

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