Phenylhydrazine → HCID 59436144, compound

HRID 1407276Notes

Reaction equation

HRID 1407276 reaction equation
C[N:2](C)[C:3]([CH3:24])=[CH:4][C:5]([C:7]1[C:12](=[O:13])[CH:11]=[CH:10][N:9]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([C:20]([F:23])([F:22])[F:21])[CH:15]=2)[N:8]=1)=O.[C:26]1([NH:32]N)[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>C(O)(=O)C>[CH3:24][C:3]1[CH:4]=[C:5]([C:7]2[C:12](=[O:13])[CH:11]=[CH:10][N:9]([C:14]3[CH:19]=[CH:18][CH:17]=[C:16]([C:20]([F:23])([F:22])[F:21])[CH:15]=3)[N:8]=2)[N:32]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[N:2]=1

Participants

4

Reactant 2

HCID 7516PhenylhydrazineHCID 66710566HCID 66710566, compound

Product 1

HCID 59436144HCID 59436144, compoundYield 16%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 3-[3-(dimethylamino)but-2-enoyl]-1-[3-(trifluoromethyl)phenyl]pyridazin-4(1H)-one (0.270 g, 0.77 mmol) and phenyl hydrazine (0.200 mL, 2.0 mmol) in acetic acid (5.0 mL) was heated under microwave conditions at 120° C. for 10 min. After this time, the reaction was cooled to room temperature and concentrated onto silica gel. The crude product purified by column chromatography (silica gel, 50:50 ethyl acetate/hexanes to ethyl acetate) to separate the two isomers, followed by preparative reverse phase HPLC and crystallization from diethyl ether to give 3-(3-methyl-1-phenyl-1H-pyrazol-5-yl)-1-[3-(trifluoromethyl)phenyl]pyridazin-4(1H)-one (0.048 g, 16%) as a white solid. 1H NMR (300 MHz, CDCl3) δ ppm 2.42 (s, 3H), 6.73 (d, J=7.9 Hz, 1H), 6.99 (dd, J=1.7, 8.1 Hz, 1H), 7.18 (br s, 1H), 7.21 (s, 1H), 7.30-7.49 (m, 6H), 7.55 (d, J=7.8 Hz, 1H), 8.19 (d, J=7.9 Hz, 1H); APCI MS m/z 397 [M+H]+; mp 167-168° C.

Workup

  1. concentrationconcentrated onto silica gel
  2. customThe crude product purified by column chromatography (silica gel, 50:50 ethyl acetate/hexanes to ethyl acetate)
  3. customto separate the two isomers
  4. customfollowed by preparative reverse phase HPLC and crystallization from diethyl ether

Sources & evidence

ORD record
ord-5a36fd1d56f94ad2bdcaea82aa6ae551
Source dataset
uspto-grants-2014_12
Patent number
US08916566B2

Reaction notes

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