Hydrochloric Acid → HCID 5875641, compound

HRID 1630764Notes

Reaction equation

HRID 1630764 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-dd45532cacd94ac89b016d27f724fd9a
Source dataset
uspto-grants-2014_07
Patent number
US08791141B2

Reaction notes

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