tert-Butyl (5-nitropyridin-2-yl)carbamate → tert-butyl N-(5-aminopyridin-2-yl)carbamate

HRID 1621672Notes

Reaction equation

HRID 1621672 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([NH:10][C:11](=[O:17])[O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[N:8][CH:9]=1)([O-])=O>CCO.[Pd]>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([NH:10][C:11](=[O:17])[O:12][C:13]([CH3:15])([CH3:14])[CH3:16])=[N:8][CH:9]=1

Participants

4

Reactant 1

HCID 11064480tert-Butyl (5-nitropyridin-2-yl)carbamate

Product 1

HCID 22064440tert-butyl N-(5-aminopyridin-2-yl)carbamateYield 98%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of tert-butyl 5-nitropyridin-2-ylcarbamate (3.76 g, 15.7 mmol) and Pd/C (Aldrich) (0.588 g, 5.52 mmol) in EtOH (100 mL) was evacuated under vacuum and refilled with hydrogen (6 times). The mixture was hydrogenated under balloon pressure of hydrogen at rt for 2.5 h. The reaction mixture was filtered through a pad of Celite® (diatomaceous earth) (eluent:EtOH) and concentrated to give tert-butyl 5-aminopyridin-2-ylcarbamate (3.22 g, 98% yield) as a cream color solid. 1H NMR (300 MHz, d6-DMSO) δ 9.06 (s, 1H); 7.62 (d, J=1.75 Hz, 1H); 7.40 (d, J=8.62 Hz, 1H); 6.94 (dd, J=8.70, 2.27 Hz, 1H); 4.93 (s, 2H); 1.44 (s, 9H). m/z (ESI, +ve ion) 210.2 (M+H)+.

Workup

  1. customwas evacuated under vacuum
  2. additionrefilled with hydrogen (6 times)
  3. filtrationThe reaction mixture was filtered through a pad of Celite® (diatomaceous earth) (eluent:EtOH)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-812f1bf2bea74d5c87bcf92b3803ea26
Source dataset
uspto-grants-2014_07
Patent number
US08772480B2

Reaction notes

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