(4'-Cyano-biphenyl-3-yl)-carbamic acid tert-butyl ester → (4'-Aminomethyl-biphenyl-3-yl)-carbamic acid tert-butyl ester

HRID 39153Notes

Reaction equation

HRID 39153 reaction equation
[C:1]([O:5][C:6](=[O:22])[NH:7][C:8]1[CH:9]=[C:10]([C:14]2[CH:19]=[CH:18][C:17]([C:20]#[N:21])=[CH:16][CH:15]=2)[CH:11]=[CH:12][CH:13]=1)([CH3:4])([CH3:3])[CH3:2]>CCO.N.O.[Ni]>[C:1]([O:5][C:6](=[O:22])[NH:7][C:8]1[CH:9]=[C:10]([C:14]2[CH:15]=[CH:16][C:17]([CH2:20][NH2:21])=[CH:18][CH:19]=2)[CH:11]=[CH:12][CH:13]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 1

HCID 67120680(4'-Cyano-biphenyl-3-yl)-carbamic acid tert-butyl ester

Product 1

HCID 59206790(4'-Aminomethyl-biphenyl-3-yl)-carbamic acid tert-butyl ester

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 702EthanolSolventHCID 12896473Azane;hydrateSolvent

Procedure

A suspension of (4′-cyano-biphenyl-3-yl)-carbamic acid tert-butyl ester (7.6 g, 26 mmol) and Raney Ni (1 g) in EtOH (500 mL) and NH3.H2O (10 mL) was hydrogenated under 50 psi of H2 at 50° C. for 6 h. The catalyst was filtered off and the filtrate was concentrated to dryness to give (4′-aminomethyl-biphenyl-3-yl)-carbamic acid tert-butyl ester, which was used directly in next step.

Workup

  1. filtrationThe catalyst was filtered off
  2. concentrationthe filtrate was concentrated to dryness

Sources & evidence

ORD record
ord-7d217eca82a542c5b4d2f1a5e11e01ee
Source dataset
uspto-grants-2013_09
Patent number
US08524767B2

Reaction notes

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