Hydrochloric Acid → HCID 67153767, compound

HRID 547862Notes

Reaction equation

HRID 547862 reaction equation
[F:1][C:2]1[C:7]([F:8])=[CH:6][C:5]([C:9]2[CH:14]=[CH:13][C:12]([O:15][CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([N+:23]([O-])=O)[CH:18]=3)=[CH:11][CH:10]=2)=[C:4]([O:26][CH3:27])[CH:3]=1.[ClH:28]>CCOC(C)=O.CCO.[Pd]>[ClH:28].[F:1][C:2]1[C:7]([F:8])=[CH:6][C:5]([C:9]2[CH:10]=[CH:11][C:12]([O:15][CH2:16][C:17]3[CH:18]=[C:19]([NH2:23])[CH:20]=[CH:21][CH:22]=3)=[CH:13][CH:14]=2)=[C:4]([O:26][CH3:27])[CH:3]=1

Participants

6

Reactant 2

HCID 313Hydrochloric AcidHCID 582877964,5-Difluoro-2-methoxy-4'-(3-nitro-benzyloxy)-biphenyl

Product 1

HCID 67153767HCID 67153767, compoundYield 95%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 4,5-difluoro-2-methoxy-4′-(3-nitro-benzyloxy)-biphenyl (300 mg, 0.808 mmol) and 10% Pd/C (45 mg) in EtOAc (2 mL), EtOH (13 mL) and 6N HCl (150 uL) was hydrogenated at 50 psi for 1.5 hrs. The reaction mixture was filtered through Celite and evaporated to dryness to give 289 mg (95%) of 3-(4′,5′-difluoro-2′-methoxy-biphenyl-4-yloxymethyl)-phenylamine hydrochloride. LC-MS (ES) calculated for C20H17F2NO2, 341.36; found m/z 342 [M+H]+.

Workup

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

Sources & evidence

ORD record
ord-254db79895374d97a2cbb2c074e740d9
Source dataset
uspto-grants-2011_05
Patent number
US07939569B1

Reaction notes

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