Serinol → 1,3-Propanediol, 2-[(6-methoxy-3-nitro-2-pyridinyl)amino]-

HRID 1824645Notes

Reaction equation

HRID 1824645 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.[NH2:13][CH:14]([CH2:17][OH:18])[CH2:15][OH:16]>C(O)C>[CH3:12][O:11][C:4]1[N:3]=[C:2]([NH:13][CH:14]([CH2:17][OH:18])[CH2:15][OH:16])[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 68294SerinolHCID 27950292-Chloro-6-methoxy-3-nitropyridine

Product 1

HCID 221417081,3-Propanediol, 2-[(6-methoxy-3-nitro-2-pyridinyl)amino]-Yield 88.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

4 g (0.0212 mol) of the product 2-chloro-3-nitro-6-methoxypyridine, 40 ml of ethanol and 3.86 g (0.042 mol) of 2-aminopropane-1,3-diol 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. 4.54 g of yellow powder are obtained, ie a yield of 88.2%.

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-48422e4d7841428d9f78bb83863d12f2
Source dataset
uspto-grants-2006_05
Patent number
US07044987B2

Reaction notes

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