(3-Chlorophenyl)hydrazine → HCID 178419962, compound

HRID 1805259Notes

Reaction equation

HRID 1805259 reaction equation
Cl[C:2]1[CH:7]=CC=C(F)[C:3]=1[C:9]1[C:13](C(OC)=O)=[C:12](C(C(=O)C(F)(F)F)=CN(C)C)[O:11][N:10]=1.ClC1C=C([NH:36][NH2:37])C=CC=1.C(N(CC)C(C)C)(C)C>C(O)C>[NH:36]1[CH:7]=[CH:2][C:3]([C:9]2[CH:13]=[CH:12][O:11][N:10]=2)=[N:37]1

Participants

5

Reactant 3

HCID 75332(3-Chlorophenyl)hydrazineHCID 81531DiisopropylethylamineHCID 3730890HCID 3730890, compound

Product 1

HCID 178419962HCID 178419962, compoundYield 225.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 0.5047 g (1.1994 mmol) methyl 3-(2-chloro-6-fluorophenyl)-5-(1-(dimethylamino)-4,4,4-trifluoro-3-oxobut-1-en-2-yl)isoxazole-4-carboxylate in dry ethanol, 0.1790 g (0.9995 mmol) 3-Chlorophenylhydrazine and 0.17 mL (0.9995 mmol) N,N-Diisopropylethylamine (DIPEA) were added. The reaction mixture was heated under reflux for 2 h. The product was isolated by using column chromatography (Petroleum ether:Diethyl ether 80:20), and 0.305 g (yield of theory: 61%) of the pyrazolyl-isoxazole derivative were obtained. Result of LC/MS [M+H]+: 499.9; 1H NMR (DMSO-d6; CCl4): 3.66 (3H, s, CH3), 7.45-7.50 (1H, dd, CH-arom.), 7.55-7.58 (1H, d, CH-arom.), 7.65-7.77 (1H, d, CH-arom.), 7.65-7.77 (1H, dd, CH-arom. phenylhydrazine), 7.65-7.77 (1H, d, CH-arom. phenylhydrazine), 7.85 (1H, s, CH-arom phenylhydrazine), 8.56 (1H, s, 1-pyrazole)

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureunder reflux for 2 h
  3. customThe product was isolated

Sources & evidence

ORD record
ord-ef8eb5c93d674f01a8aa54cf900f98ef
Source dataset
uspto-grants-2013_01
Patent number
US08354436B2

Reaction notes

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