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

HRID 450175Notes

Reaction equation

HRID 450175 reaction equation
[C:1]([O:5][C:6](=[O:17])[NH:7][C:8]1[CH:13]=[CH:12][C:11]([N+:14]([O-])=O)=[CH:10][N:9]=1)([CH3:4])([CH3:3])[CH3:2]>C1COCC1.CO.[Pd]>[NH2:14][C:11]1[CH:12]=[CH:13][C:8]([NH:7][C:6](=[O:17])[O:5][C:1]([CH3:3])([CH3:2])[CH3:4])=[N:9][CH:10]=1

Participants

4

Reactant 1

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

Product 1

HCID 22064440tert-butyl N-(5-aminopyridin-2-yl)carbamateYield 101.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21899815MeOH tetrahydrofuranSolvent

Procedure

To 0.314 g (1.31 mmol) of the above nitro compound in THF-MeOH (16 mL, 1:1) was added 0.460 g of 10% Pd/C and the mixture was stirred under hydrogen (40 in/Hg) for 4 hrs. The reaction mixture was filtered through celite, washed with MeOH and concentrated to give 0.277 g (99% yield) of tert-butyl 5-aminopyridin-2-yl-carbamate as a white powder: 1H NMR (DMSO-d6) δ9.00 (br s, 1H), 7.62 (dd, J=2.7, 0.4 Hz, 1H), 7.39 (d, J=8.7 Hz, 1H), 6.94 (dd, J=8.7, 2.8 Hz, 1H), 4.92 (s, 2H), 1.44 (s, 9H).

Workup

  1. filtrationThe reaction mixture was filtered through celite
  2. washwashed with MeOH
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-0ba0fb49e073481883f49ac2b290b217
Source dataset
uspto-grants-2013_07
Patent number
US08486939B2

Reaction notes

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