Sodium Hydroxide → HCID 86625747, compound

HRID 2068754Notes

Reaction equation

HRID 2068754 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[N:5]=[C:4]([N:9]2[CH2:14][CH2:13][O:12][CH2:11][CH2:10]2)[CH:3]=1.[N+:15]([O-])([O-:17])=[O:16].[K+].[OH-].[Na+]>S(=O)(=O)(O)O>[Cl:1][C:2]1[C:7]([N+:15]([O-:17])=[O:16])=[C:6]([Cl:8])[N:5]=[C:4]([N:9]2[CH2:10][CH2:11][O:12][CH2:13][CH2:14]2)[CH:3]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 24434Potassium NitrateHCID 596738604-(4,6-Dichloropyridin-2-yl)morpholine

Product 1

HCID 86625747HCID 86625747, compoundYield 49%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

To a solution of 4-(4,6-dichloropyridin-2-yl)-morpholine (3.90 g) in concentrated sulfuric acid (40 mL) was added potassium nitrate (1.80 g) over 10 minutes. The reaction mixture was stirred for 16 hours at ambient temperature and then poured in to chrushed ice (500 g). The reaction mixture was made alkaline with concentrated sodium hydroxide and extracted with ethyl acetate (2×100 mL). The combined organic phases were dried over magnesium sulfate and concentrated in vacuo. The crude product was subjected to flash chromatography (SiO2, heptane/ethylacetate 3:1) to furnish 2.26 g (49% yield) of the title compound as a yellow solid. LC-MS (n/z) 278.0 (M+); tR=3.10, (UV, ELSD) 96.5%, 98.8%. 1H NMR (500 MHz, CDCl3): 3.62 (m, 4H), 3.80 (m, 4H), 6.50 (s, 1H).

Workup

  1. extractionextracted with ethyl acetate (2×100 mL)
  2. dry with materialThe combined organic phases were dried over magnesium sulfate
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a48a88eac04340689e7397d36e889113
Source dataset
uspto-grants-2012_10
Patent number
US08299071B2

Reaction notes

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