[6-(4-Cyano-phenyl)-pyridin-2-yl]carbamic acid tert-butyl ester → [6-(4-Aminomethyl-phenyl)-pyridin-2-yl]-carbamic acid

HRID 1505136Notes

Reaction equation

HRID 1505136 reaction equation
C([O:5][C:6](=[O:22])[NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([C:14]2[CH:19]=[CH:18][C:17]([C:20]#[N:21])=[CH:16][CH:15]=2)[N:9]=1)(C)(C)C>CCO.N.O.[Ni]>[NH2:21][CH2:20][C:17]1[CH:18]=[CH:19][C:14]([C:10]2[N:9]=[C:8]([NH:7][C:6](=[O:5])[OH:22])[CH:13]=[CH:12][CH:11]=2)=[CH:15][CH:16]=1

Participants

5

Reactant 1

HCID 67133691[6-(4-Cyano-phenyl)-pyridin-2-yl]carbamic acid tert-butyl ester

Product 1

HCID 86674909[6-(4-Aminomethyl-phenyl)-pyridin-2-yl]-carbamic acid

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 702EthanolSolventHCID 12896473Azane;hydrateSolvent

Procedure

A suspension of [6-(4-cyano-phenyl)-pyridin-2-yl]carbamic acid tert-butyl ester (7.0 g, 24 mmol), Raney Ni (1.0 g) in EtOH (500 mL) and NH3.H2O (10 mL) was hydrogenated under H2 (50 psi.) at 50° C. for 6 h. The catalyst was filtered off and the filtrate was concentrated to dryness to give [6-(4-aminomethyl-phenyl)-pyridin-2-yl]-carbamic acid ten-butyl ester, which was used directly in next step. 1H NMR (300 MHz, CDCl3) δ 7.83-7.92 (m, 3 H), 7.70 (t, J=7.8 Hz, 1 H), 7.33-7.40 (m, 4 H), 3.92 (brs, 2 H), 1.53 (s, 9 H).

Workup

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

Sources & evidence

ORD record
ord-9c82c2e58b584df6817a4183aa64d525
Source dataset
uspto-grants-2015_12
Patent number
US09216969B2

Reaction notes

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