Hydrochloric Acid → HCID 70816631, compound

HRID 1842896Notes

Reaction equation

HRID 1842896 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:19][CH3:20])=[C:6]([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:7]=1.CCOCC.Cl.C(Cl)(Cl)Cl.CO>C1COCC1>[ClH:1].[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:19][CH3:20])=[C:6]([N:8]2[C:12]([CH2:13][NH2:14])=[CH:11][C:10]([C:15]([F:16])([F:17])[F:18])=[N:9]2)[CH:7]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 21584188Chloroform methanolHCID 70816662HCID 70816662, compound

Product 1

HCID 70816631HCID 70816631, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred solution of 1-(5-chloro-2-methoxyphenyl)-3-(trifluoromethyl)-1H-pyrazole-5-carbonitrile (3.09 g, 10.27 mmol, 1.0 eq) in THF (40 mL) was added BH3-DMS (2.30 g, 30.81 mmol, 3.0 eq) at 0° C. and heated to reflux for 1 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 the mixture 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-(5-chloro-2-methoxyphenyl)-3-(trifluoromethyl)-1H-pyrazol-5-yl)methanamine hydrochloride (1.3 g, 20% yield over 3 steps) as white solid (TLC system: CHCl3/MeOH (9:1), Rf 0.5).

Workup

  1. temperatureheated
  2. temperatureto reflux for 1 h
  3. customquenched with 1N HCl
  4. extractionthe mixture extracted with ethyl acetate (100 mL×2)
  5. dry with materialdried (Na2SO4)
  6. customthe solvent evaporated
  7. customto get a pale yellow oil

Sources & evidence

ORD record
ord-01a4fd3238ed4444af1d3a7b36fdbc31
Source dataset
uspto-grants-2015_02
Patent number
US08946204B2

Reaction notes

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