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

HRID 1852700Notes

Reaction equation

HRID 1852700 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. Preparative Example 2.3 4,6-dichloro-3-((trans-4-methylcyclohexyl)methyl)-3H-imidazo[4,5-c]pyridine

Workup

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

Sources & evidence

ORD record
ord-4a9398b46ba04675b3cf0a4b4d405000
Source dataset
uspto-grants-2015_02
Patent number
US08962611B2

Reaction notes

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