Hydrochloric Acid → [2-Quinolin-4-yl-1-(3-trifluoromethyl-phenyl)-ethylidene]-hydrazine

HRID 8227Notes

Reaction equation

HRID 8227 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([CH2:11][C:12]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([C:20]([F:23])([F:22])[F:21])[CH:15]=2)=O)=[CH:3][CH:2]=1.[NH2:24][NH2:25].Cl>C(O)C>[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([CH2:11][C:12](=[N:24][NH2:25])[C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([C:20]([F:23])([F:22])[F:21])[CH:15]=2)=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 9321HydrazineHCID 118340212-Quinolin-4-yl-1-(3-trifluoromethyl-phenyl)-ethanone

Product 1

HCID 73858336[2-Quinolin-4-yl-1-(3-trifluoromethyl-phenyl)-ethylidene]-hydrazine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 2-quinolin-4-yl-1-(3-trifluoromethyl-phenyl)-ethanone (1.0 g, 3.2 mmol) in ethanol (13 mL) is cooled to 0° C. and treated with hydrazine (0.6 g, 19 mmol) and concentrated hydrochloric acid (0.13 mL, 1.6 mmol). The mixture is refluxed for 2 h and concentrated in vacuo. The residue is taken up in dichloromethane and washed with saturated sodium bicarbonate (30 mL), water (2×30 mL), and brine (30 mL). The solution is dried over anhydrous sodium sulfate and filtered. The filtrate is concentrated to yield the title compound, 1.0 g (97%), as a pale yellow foam.

Workup

  1. temperatureThe mixture is refluxed for 2 h
  2. concentrationconcentrated in vacuo
  3. washwashed with saturated sodium bicarbonate (30 mL), water (2×30 mL), and brine (30 mL)
  4. dry with materialThe solution is dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationThe filtrate is concentrated

Sources & evidence

ORD record
ord-a72c5d993d8b483c94f70f3134fc65f0
Source dataset
uspto-grants-2006_08
Patent number
US07087626B2

Reaction notes

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