Tert-butyl (2,6-dichloro-3-nitropyridin-4-yl)carbamate → Tert-butyl (3-amino-2,6-dichloropyridin-4-yl)carbamate

HRID 81093Notes

Reaction equation

HRID 81093 reaction equation
[Cl:1][C:2]1[C:7]([N+:8]([O-])=O)=[C:6]([NH:11][C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])[CH:5]=[C:4]([Cl:19])[N:3]=1>C(O)C.O.[Fe]>[NH2:8][C:7]1[C:2]([Cl:1])=[N:3][C:4]([Cl:19])=[CH:5][C:6]=1[NH:11][C:12](=[O:18])[O:13][C:14]([CH3:15])([CH3:16])[CH3:17]

Participants

5

Reactant 1

HCID 86671448Tert-butyl (2,6-dichloro-3-nitropyridin-4-yl)carbamate

Product 1

HCID 86724467Tert-butyl (3-amino-2,6-dichloropyridin-4-yl)carbamate

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A mixture of tert-butyl (2,6-dichloro-3-nitropyridin-4-yl)carbamate (700 g, 2.27 mol) and iron (1272.7 g, 22.7 mol) in ethanol (5 L) and water (1 L) was stirred at room temperature for 10 h. The mixture was filtered, the filtrate was concentrated in vacuo, and the crude product was crystallized using EtOAc to give tert-butyl (3-amino-2,6-dichloropyridin-4-yl)carbamate.

Workup

  1. filtrationThe mixture was filtered
  2. concentrationthe filtrate was concentrated in vacuo
  3. customthe crude product was crystallized

Sources & evidence

ORD record
ord-7057e44afc3840a58f7b467c63e2741f
Source dataset
uspto-grants-2014_09
Patent number
US08846657B2

Reaction notes

Loading…