2-Chloro-3-nitropyridine → N-(4-methoxybutyl)-3-nitropyridin-2-amine

HRID 2168907Notes

Reaction equation

HRID 2168907 reaction equation
Cl[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=1.Cl.[CH3:12][O:13][CH2:14][CH2:15][CH2:16][CH2:17][NH2:18].C(N(C(C)C)CC)(C)C>CC(O)C>[CH3:12][O:13][CH2:14][CH2:15][CH2:16][CH2:17][NH:18][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 796132-Chloro-3-nitropyridineHCID 81531DiisopropylethylamineHCID 457923494-Methoxybutan-1-amine hydrochloride

Product 1

HCID 58355169N-(4-methoxybutyl)-3-nitropyridin-2-amineYield 84.7%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

2-Chloro-3-nitropyridine (3.54 g) and 4-methoxybutan-1-amine hydrochloride (3.12 g) were suspended in 2-propanol (100 ml), diisopropylethylamine (11.6 μl) was added and the mixture was heated under reflux with stirring for 4 days. The reaction mixture was cooled to room temperature, and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography, and a fraction eluted with ethyl acetate-hexane (3:7) was concentrated under reduced pressure to give the object product (4.26 g).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux
  3. concentrationconcentrated under reduced pressure
  4. washa fraction eluted with ethyl acetate-hexane (3:7)
  5. concentrationwas concentrated under reduced pressure

Sources & evidence

ORD record
ord-f2ddd509441240ef8ad9b34fbb81cd94
Source dataset
uspto-grants-2015_06
Patent number
US09045436B2

Reaction notes

Loading…