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

HRID 1812084Notes

Reaction equation

HRID 1812084 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-385ce3d5b67d46a69609a01b3d4eb924
Source dataset
uspto-grants-2013_01
Patent number
US08362241B2

Reaction notes

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