o-Tolylhydrazinium(1+) chloride → 3-(4-fluoro-2-methylphenyl)-1-(2-methylphenyl)-1H-pyrazol-5-amine

HRID 915564Notes

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=O)[CH2:9][C:10]#[N:11])=[C:4]([CH3:13])[CH:3]=1.Cl.[CH3:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[NH:22][NH2:23]>C1(C)C=CC=CC=1>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[C:10]([NH2:11])[N:22]([C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=3[CH3:15])[N:23]=2)=[C:4]([CH3:13])[CH:3]=1

Participants

Conditions

Temperature: 110 °C

Procedure

To a solution of 3-(4-fluoro-2-methylphenyl)-3-oxopropanenitrile (2.0 g, 11.3 mmol) in toluene (10 mL) was added (2-methylphenyl)hydrazine hydrochloride (2.15 g, 13.5 mmol). The reaction was stirred at 110° C. for 16 h, and then cooled to rt. It was concentrated under reduced pressure, and the residue was purified by silica gel flash chromatography (2:1-1:1=hexanes:ethyl acetate) to afford the product as a yellow oil (500 mg, 16%). 1H NMR (400 MHz, DMSO-d6) δ 2.12 (s, 3H), 2.44 (s, 3H), 5.74 (s, 1H), 7.02-7.14 (m, 2H), 7.34-7.43 (m, 4H), 7.52 (dd, 1H); ES-MS m/z 282.4 (MH+); HPLC RT (min) 3.36

Workup

temperaturecooled to rt
concentrationIt was concentrated under reduced pressure
customthe residue was purified by silica gel flash chromatography (2:1-1:1=hexanes:ethyl acetate)

Sources & evidence

ORD record: ord-53987f0d620841438055ddc4e3e4db93
Source dataset: uspto-grants-2007_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07265144B2

Reaction notes

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