Hydrochloric Acid → 3-(2',4',5'-Trifluoro-biphenyl-4-yloxymethyl)-phenylamine hydrochloride

HRID 547860Notes

Reaction equation

HRID 547860 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([F:9])=[CH:4][C:3]=1[C:10]1[CH:15]=[CH:14][C:13]([O:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([N+:24]([O-])=O)[CH:19]=2)=[CH:12][CH:11]=1.[ClH:27]>CCOC(C)=O.CCO.[Pd]>[ClH:27].[F:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([F:9])=[CH:4][C:3]=1[C:10]1[CH:15]=[CH:14][C:13]([O:16][CH2:17][C:18]2[CH:19]=[C:20]([NH2:24])[CH:21]=[CH:22][CH:23]=2)=[CH:12][CH:11]=1

Participants

6

Reactant 2

HCID 313Hydrochloric AcidHCID 58287797HCID 58287797, compound

Product 1

HCID 671537603-(2',4',5'-Trifluoro-biphenyl-4-yloxymethyl)-phenylamine hydrochloride

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 2,4,5-trifluoro-4′-(3-nitro-benzyloxy)-biphenyl (150 mg, 0.418 mmol) and 10% Pd/C (40 mg) in EtOAc (2 mL), EtOH (10 mL) and 6N HCl (100 uL) was hydrogenated at 50 psi for 1.25 hrs. The reaction mixture was filtered through Celite and evaporated to dryness to give 3-(2′,4′,5′-trifluoro-biphenyl-4-yloxymethyl)-phenylamine hydrochloride. LC-MS (ES) calculated for C19H14F3NO, 329.32; found m/z 330 [M+H]+.

Workup

  1. filtrationThe reaction mixture was filtered through Celite
  2. customevaporated to dryness

Sources & evidence

ORD record
ord-414057368e5240a7ace24cd2a40016bf
Source dataset
uspto-grants-2011_05
Patent number
US07939569B1

Reaction notes

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