HCID 570528, compound → 4-Amino-2-ethylpyridine

HRID 1529206Notes

Reaction equation

HRID 1529206 reaction equation
[CH2:1]([C:3]1[CH:8]=[C:7]([N+:9]([O-])=O)[CH:6]=[CH:5][N+:4]=1[O-])[CH3:2]>CCO.[NH4+].[Cl-].C(Cl)Cl.CO.[Fe]>[CH2:1]([C:3]1[CH:8]=[C:7]([NH2:9])[CH:6]=[CH:5][N:4]=1)[CH3:2]

Participants

6

Reactant 1

HCID 570528HCID 570528, compound

Product 1

HCID 120153664-Amino-2-ethylpyridine

Reagents, catalysts & solvents 4

HCID 23925IronCatalystHCID 702EthanolSolventHCID 25517Ammonium ChlorideSolventHCID 21226129Dichloromethane methanolSolvent

Procedure

A solution of 388.0 g (2.3 mol) 2-ethyl-4-nitro-pyridine-1-oxide in 3.0 L EtOH and 1.0 L saturated NH4Cl solution (1.0 L) is stirred with 647.5 g (11.6 mol) iron powder. This mixture is refluxed for 3 h. The iron powder is filtered off with Celite®, and the solvent is removed from the filtrate in vaccuo to afford a crude oil. This oil is diluted with DCM/MeOH (1.0 L, 10:1) and the undissolved NH4Cl is removed by filtration, the filtrate is dried in vaccuo to afford the title compound. Yield: 200.0 g (71%).

Workup

  1. temperatureThis mixture is refluxed for 3 h
  2. filtrationThe iron powder is filtered off with Celite®
  3. customthe solvent is removed from the filtrate in vaccuo
  4. customto afford a crude oil
  5. customthe undissolved NH4Cl is removed by filtration
  6. customthe filtrate is dried in vaccuo

Sources & evidence

ORD record
ord-f29190e89d77494f82a5538331f0ebda
Source dataset
uspto-grants-2015_07
Patent number
US09090564B2

Reaction notes

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