Sodium Methoxide → HCID 66862671, compound

HRID 1158616Notes

Reaction equation

HRID 1158616 reaction equation
[Cl:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[C:6](Cl)[N:5]=[C:4]([N:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)[CH:3]=1.[CH3:18][O-:19].[Na+]>CO>[Cl:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[C:6]([O:19][CH3:18])[N:5]=[C:4]([N:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)[CH:3]=1

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 86625747HCID 86625747, compound

Product 1

HCID 66862671HCID 66862671, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
65 °C

Procedure

To a solution of 4-(4,6-dichloro-5-nitropyridin-2-yl)-morpholine (2.02 g) in methanol (15 ml) was added sodium methoxide (0.98 g) and the mixture was heated for 16 hours at 65° C. After cooling to ambient temperature the reaction mixture was concentrated in vacuo. The crude product was subjected to flash chromatography (SiO2, heptane/ethylacetate 3:1) to furnish 0.89 g (45% yield) of 4-(4-chloro-6-methoxy-5-nitropyridin-2-yl)-morpholine (fast eluting band) and 0.38 g (19%) of 4-(6-chloro-4-methoxy-5-nitropyridin-2-yl)-morpholine (late eluting band), both as yellow solids.

Workup

  1. temperatureAfter cooling to ambient temperature the reaction mixture
  2. concentrationwas concentrated in vacuo

Sources & evidence

ORD record
ord-6eecdb9a60084a4f97bfe1f2188f563d
Source dataset
uspto-grants-2010_10
Patent number
US07812020B2

Reaction notes

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