Hydrochloric Acid → 1-Amino-2-(3'-hydroxybiphenyl-2-yl)ethane hydrochloride

HRID 278179Notes

Reaction equation

HRID 278179 reaction equation
C([O:8][C:9]1[CH:10]=[C:11]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[CH2:21][C:22]#[N:23])[CH:12]=[CH:13][CH:14]=1)C1C=CC=CC=1.[ClH:24]>CO.[Pd]>[ClH:24].[NH2:23][CH2:22][CH2:21][C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=1[C:11]1[CH:12]=[CH:13][CH:14]=[C:9]([OH:8])[CH:10]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 22627114(3'-Benzyloxybiphenyl-2-yl)acetonitrile

Product 1

HCID 226270951-Amino-2-(3'-hydroxybiphenyl-2-yl)ethane hydrochloride

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of (3′-benzyloxybiphenyl-2-yl)acetonitrile from Step B (140 mg, 0.47 mmol), conc. HCl (0.060 mL, 0.73 mmol), and 10% Pd-C (30 mg) in MeOH (15 mL) was shaken under an atmosphere of hydrogen (ca. 50 atm) for 48 hours. The reaction mixture was filtered through a celite pad, washing with MeOH, and the filtrate was concentrated under reduced pressure to give the titled product, which was sufficiently pure for use in the next step.

Workup

  1. filtrationThe reaction mixture was filtered through a celite pad
  2. washwashing with MeOH
  3. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-e27dcf86431340299758016989f5cf5e
Source dataset
uspto-grants-2002_03
Patent number
US06358985B1

Reaction notes

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