Ethanol → 3-Trifluoromethylbenzoic acid [1-(3-pyridinyl)propylidene]hydrazide

HRID 1493715Notes

Reaction equation

HRID 1493715 reaction equation
[F:1][C:2]([F:14])([F:13])[C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][CH:12]=1)[C:6]([NH:8][NH2:9])=[O:7].[CH2:15]([C:17]([C:19]1[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=1)=O)[CH3:16].C(O)C>C(O)(=O)C.O>[N:21]1[CH:22]=[CH:23][CH:24]=[C:19]([C:17](=[N:9][NH:8][C:6](=[O:7])[C:5]2[CH:10]=[CH:11][CH:12]=[C:3]([C:2]([F:13])([F:14])[F:1])[CH:4]=2)[CH2:15][CH3:16])[CH:20]=1

Participants

6

Reactant 3

HCID 702EthanolHCID 740741-(3-Pyridyl)propan-1-oneHCID 27774173-(Trifluoromethyl)benzoic acid hydrazide

Product 1

HCID 540455043-Trifluoromethylbenzoic acid [1-(3-pyridinyl)propylidene]hydrazideYield 74%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 962WaterSolvent

Procedure

A mixture of 10.21 gm (0.05 mole) of 3-trifluoromethylbenzoic acid hydrazide, 6.76 gm (0.05 mole) of ethyl-3-pyridyl ketone, 10 drops of glacial acetic acid and 100 ml of absolute ethanol was refluxed 15 hr. The reaction mixture was diluted with water to the cloud point and cooled at room temperature than chilled in the refrigerator. The solids that separated were collected, washed with Skellysolve B and dried to give 11.88 gm (74%) of product having a melting point of 119.4° C.

Workup

  1. temperaturewas refluxed 15 hr
  2. temperaturethan chilled in the refrigerator
  3. customThe solids that separated
  4. customwere collected
  5. washwashed with Skellysolve B
  6. customdried

Sources & evidence

ORD record
ord-182e52733ba746e1ae8c58aced55713f
Source dataset
uspto-grants-1991_06
Patent number
US05023334

Reaction notes

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