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

HRID 1502170Notes

Reaction equation

HRID 1502170 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>CC(O)=O.[Zn]>[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)carbamate

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Procedure

tert-Butyl 5-nitropyridin-2-ylcarbamate (750 mg, 3.14 mmol) was suspended in AcOH at RT with vigorously stirring. Zinc (2051 mg, 31.4 mmol) was added slowly (exothermic reaction). The mixture was stirred at RT for 20 min, and filtered. The filter cake was washed with ethyl acetate. The filtrate was concentrated to give tert-butyl 5-aminopyridin-2-ylcarbamate: LC/MS: [(M+1-56)]+=154.16.

Workup

  1. custom(exothermic reaction)
  2. stirringThe mixture was stirred at RT for 20 min
  3. filtrationfiltered
  4. washThe filter cake was washed with ethyl acetate
  5. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-3008d110058c4464b0f79ede1b00bf10
Source dataset
uspto-grants-2015_12
Patent number
US09206199B2

Reaction notes

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