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

HRID 38144Notes

Reaction equation

HRID 38144 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]1[CH:14]=[CH:13][C:12]([N+:15]([O-])=O)=[CH:11][N:10]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>CO.C(OCC)(=O)C.[Pd]>[NH2:15][C:12]1[CH:13]=[CH:14][C:9]([NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])=[N:10][CH:11]=1

Participants

5

Reactant 1

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

Product 1

HCID 22064440tert-butyl N-(5-aminopyridin-2-yl)carbamateYield 97%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a suspension of (tert-butoxy)-N-(5-nitro(2-pyridyl))carboxamide (0.27 g, 1.13 mmol) in methanol (2 mL), ethyl acetate (4 mL) and TEA (0.16 mL) was added 10% Pd/C (60 mg, 0.056 mmol) under argon. The reaction mixture was hydrogenated under 1 atm H2 for 20 hr, filtered through Celite and concentrated in vacuo to give N-(5-amino(2-pyridyl))(tert-butoxy)carboxamide (0.226 g, 97%). 1H-NMR (DMSO-d6): δ 1.40 (s, 9H), 4.92 (br s, 2H), 6.89-6.91 (dd, 1H), 7.35-7.37 (d, 1H), 7.58 (d, 1H), 9.06 (s, 1H).

Workup

  1. filtrationfiltered through Celite
  2. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-bec66c3b19514dca85015b8b0c74dbf5
Source dataset
uspto-grants-2013_09
Patent number
US08524721B2

Reaction notes

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