3-(Methylamino)propane-1,2-diol → 3-[(6-Methoxy-3-nitro-2-pyridyl)methylamino]propane-1,2-diol

HRID 1292704Notes

Reaction equation

HRID 1292704 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.[CH3:13][NH:14][CH2:15][CH:16]([OH:19])[CH2:17][OH:18]>C(O)C>[CH3:12][O:11][C:4]1[N:3]=[C:2]([CH2:13][NH:14][CH2:15][CH:16]([OH:19])[CH2:17][OH:18])[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 27341223-(Methylamino)propane-1,2-diolHCID 27950292-Chloro-6-methoxy-3-nitropyridine

Product 1

HCID 694175053-[(6-Methoxy-3-nitro-2-pyridyl)methylamino]propane-1,2-diolYield 87.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

4 g (0.0219 mol) of the product 2-chloro-3-nitro-6-methoxypyridine, 50 ml of ethanol and 4.15 ml (0.0438 mol) of 3-methylamino-1,2-dihydroxypropane 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. 4.74 g of yellow powder are obtained, ie a yield of 87.1%.

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-5e4504704ed9444f96b6857ac121ab98
Source dataset
uspto-grants-2007_07
Patent number
US07238211B2

Reaction notes

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