Hydrochloric Acid → (1-(3-chloro-2-methoxyphenyl)-3-(trifluoromethyl)-1H-pyrazol-5-yl)methanamine hydrochloride

HRID 1842892Notes

Reaction equation

[Cl:1][C:2]1[C:3]([O:19][CH3:20])=[C:4]([N:8]2[C:12]([C:13]#[N:14])=[CH:11][C:10]([C:15]([F:18])([F:17])[F:16])=[N:9]2)[CH:5]=[CH:6][CH:7]=1.CCOCC.Cl.C(Cl)(Cl)Cl.CO>C1COCC1>[ClH:1].[Cl:1][C:2]1[C:3]([O:19][CH3:20])=[C:4]([N:8]2[C:12]([CH2:13][NH2:14])=[CH:11][C:10]([C:15]([F:17])([F:18])[F:16])=[N:9]2)[CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a stirred solution of 1-(3-chloro-2-methoxyphenyl)-3-(trifluoromethyl)-1H-pyrazole-5-carbonitrile (2.03 g, 6.74 mmol, 1.0 eq) in THF (20 mL) was added BH3-DMS (0.512 g, 6.74 mmol, 1.0 eq) at 0° C. and heated to reflux for 3 h. The reaction mixture was cooled to 0° C. and quenched with 1N HCl and basified with 1N solution of NaOH to a pH of ˜10 and extracted with ethyl acetate (100 mL×2), dried (Na2SO4), the solvent evaporated to get a pale yellow oil. The oil was treated with ether and HCl to get (1-(3-chloro-2-methoxyphenyl)-3-(trifluoromethyl)-1H-pyrazol-5-yl)methanamine hydrochloride (0.20, 6% yield over 3 steps) as an off white solid (TLC system: CHCl3/MeOH (9:1), Rf 0.5).

Workup

temperatureheated
temperatureto reflux for 3 h
customquenched with 1N HCl
extractionextracted with ethyl acetate (100 mL×2)
dry with materialdried (Na2SO4)
customthe solvent evaporated
customto get a pale yellow oil

Sources & evidence

ORD record: ord-6b57c44b1a00442bab84e5f32e112adc
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08946204B2

Reaction notes

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