Allylamine → Allyl-(3-nitropyridin-4-yl)amine

HRID 2112909Notes

Reaction equation

HRID 2112909 reaction equation
[CH2:1]([NH2:4])[CH:2]=[CH2:3].Cl.C(O[C:9]1[CH:14]=[CH:13][N:12]=[CH:11][C:10]=1[N+:15]([O-:17])=[O:16])C>C(O)C>[CH2:1]([NH:4][C:9]1[CH:14]=[CH:13][N:12]=[CH:11][C:10]=1[N+:15]([O-:17])=[O:16])[CH:2]=[CH2:3]

Participants

4

Reactant 2

HCID 7853AllylamineHCID 124074974-Ethoxy-3-nitropyridine--hydrogen chloride (1/1)

Product 1

HCID 23070628Allyl-(3-nitropyridin-4-yl)amine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Allyl amine (40 mL) was added to a solution of 4-ethoxy-3-nitropyridine hydrochloride [CAS No. 94602-04-7] (18.0 g) in ethanol (400 mL), and this was heated under reflux for eight hours. The reaction solution was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography. The fraction eluted by ethyl acetate-hexane (1:1) gave the title compound (13.6 g).

Workup

  1. temperatureunder reflux for eight hours
  2. concentrationThe reaction solution was concentrated under reduced pressure
  3. customthe residue was purified by silica gel column chromatography
  4. washThe fraction eluted by ethyl acetate-hexane (1:1)

Sources & evidence

ORD record
ord-b1284af7c671471987f95206590abe28
Source dataset
uspto-grants-2009_04
Patent number
US07524847B2

Reaction notes

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