N-(2-aminoethyl)acetamide → N-[2-[(6-Methoxy-3-nitro-2-pyridinyl)amino]ethyl]acetamide

HRID 1824647Notes

Reaction equation

HRID 1824647 reaction equation
Cl[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[C:4]([O:11][CH3:12])[N:3]=1.[C:13]([NH:16][CH2:17][CH2:18][NH2:19])(=[O:15])[CH3:14]>C(O)C>[CH3:12][O:11][C:4]1[N:3]=[C:2]([NH:19][CH2:18][CH2:17][NH:16][C:13](=[O:15])[CH3:14])[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 66082N-(2-aminoethyl)acetamideHCID 27950292-Chloro-6-methoxy-3-nitropyridine

Product 1

HCID 22141713N-[2-[(6-Methoxy-3-nitro-2-pyridinyl)amino]ethyl]acetamideYield 72.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

4 g (0.0212 mol) of the product 2-chloro-3-nitro-6-methoxypyridine, 50 ml of ethanol and 4.51 ml (0.0424 mol) of N-acetylethane-1,2-diamine are placed in a fully equipped round-bottomed flask. The mixture is refluxed for 2 hours with stirring and is then poured onto an ice/water mixture with stirring. The precipitate formed is filtered off by suction and dried under vacuum to constant weight. 3.9 g of yellow powder are obtained, ie a yield of 72.5%.

Workup

  1. temperatureThe mixture is refluxed for 2 hours
  2. stirringwith stirring
  3. customThe precipitate formed
  4. filtrationis filtered off by suction
  5. customdried under vacuum to constant weight

Sources & evidence

ORD record
ord-6fb14b6f9be342ab94105b8f89c2007f
Source dataset
uspto-grants-2006_05
Patent number
US07044987B2

Reaction notes

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