(3-Chlorophenyl)hydrazine → HCID 178419962, compound

HRID 1805260Notes

Reaction equation

HRID 1805260 reaction equation
Cl[C:2]1[CH:7]=CC=C(F)[C:3]=1[C:9]1[C:13](C#N)=[C:12](/C(/C(=O)C(F)(F)F)=C/N(C)C)[O:11][N:10]=1.ClC1C=C([NH:34][NH2:35])C=CC=1.CCN(C(C)C)C(C)C>C(O)C>[NH:34]1[CH:7]=[CH:2][C:3]([C:9]2[CH:13]=[CH:12][O:11][N:10]=2)=[N:35]1

Participants

5

Reactant 3

HCID 75332(3-Chlorophenyl)hydrazineHCID 81531DiisopropylethylamineHCID 68153171HCID 68153171, compound

Product 1

HCID 178419962HCID 178419962, compoundYield 10.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 0.1 g (0.2579 mmol) (Z)-3-(2-chloro-6-fluorophenyl)-5-(1-(dimethylamino)-4,4,4-trifluoro-3-oxobut-1-en-2-yl)isoxazole-4-carbonitrile in dry ethanol, 0.0462 g (0.2579 mmol) 3-Chlorophenylhydrazine and 0.78 mL (0.2579 mmol) DIPEA were added. The reaction mixture was heated under reflux for 3 h. The mixture was concentrated in vacuo and was dried in high vacuum. Purification was achieved by using pTLC, and 0.0037 g (yield of theory: 3.0%) of the pyrazolyl-isoxazole derivativewere obtained. Result of LC/MS MH+: 466.9; 1H NMR (DMSO-d6; CCl4): 7.73-7.97 (6H, m, CH-arom.), 8.04 (1H, s, CH-arom.), 8.81 (1H, s, CH-pyraz.)

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureunder reflux for 3 h
  3. concentrationThe mixture was concentrated in vacuo
  4. customwas dried in high vacuum
  5. customPurification

Sources & evidence

ORD record
ord-e460095a74fd49a9926dbb9a209d5b6c
Source dataset
uspto-grants-2013_01
Patent number
US08354436B2

Reaction notes

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