Hydrochloric Acid → [1,1′-Biphenyl]-4-methanamine, 4′-(trifluoromethoxy)-, hydrochloride (1:1)

HRID 1855623Notes

Reaction equation

HRID 1855623 reaction equation
[F:1][C:2]([F:19])([F:18])[O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:15]=[CH:14][C:13]([C:16]#[N:17])=[CH:12][CH:11]=2)=[CH:6][CH:5]=1.FC(F)(F)OC1C=CC(B(O)O)=CC=1.[ClH:34]>C(O)C.[OH-].[OH-].[Pd+2]>[ClH:34].[F:1][C:2]([F:18])([F:19])[O:3][C:4]1[CH:5]=[CH:6][C:7]([C:10]2[CH:15]=[CH:14][C:13]([CH2:16][NH2:17])=[CH:12][CH:11]=2)=[CH:8][CH:9]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 27343864-(Trifluoromethoxy)phenylboronic acidHCID 214636134-[4-(Trifluoromethoxy)phenyl]benzonitrile

Product 1

HCID 22928457[1,1′-Biphenyl]-4-methanamine, 4′-(trifluoromethoxy)-, hydrochloride (1:1)

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Procedure

A solution of 4′-[(trifluoromethyl)oxy]-4-biphenylcarbonitrile (prepared from {4-[(trifluoromethyl)oxy]phenyl}boronic acid by a method analogous to that described for the 4′-trifluoromethyl analogue, Intermediate D6 of WO 02/30911) (66.6 g) in ethanol (2000 ml) and concentrated hydrochloric acid (100 ml) was hydrogenated over Pearlman's catalyst (10 g) at 25 psi until reduction was complete. The catalyst was removed by filtration through celite, then the solvent was removed in vacuo to obtain the desired product.

Workup

  1. customThe catalyst was removed by filtration through celite
  2. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-417e4b42768a406f93aa27a34c23b9a3
Source dataset
uspto-grants-2015_02
Patent number
US08962633B2

Reaction notes

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