Ammonium Chloride → HCID 64206275, compound

HRID 712670Notes

Reaction equation

HRID 712670 reaction equation
[Br:1][C:2]1[CH:3]=[N+:4]([O-])[CH:5]=[C:6]([O:8][CH2:9][CH2:10][CH2:11][S:12]([CH3:15])(=[O:14])=[O:13])[CH:7]=1.[NH4+].[Cl-]>CCO.[Fe]>[Br:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([O:8][CH2:9][CH2:10][CH2:11][S:12]([CH3:15])(=[O:13])=[O:14])[CH:7]=1

Participants

5

Reactant 2

HCID 25517Ammonium ChlorideHCID 117667317HCID 117667317, compound

Product 1

HCID 64206275HCID 64206275, compoundYield 32.7%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

To a mixture of 3-bromo-5-(3-methanesulfonyl-propoxy)-pyridine 1-oxide (800 mg, 2.6 mmol) and saturated NH4Cl aqueous solution (3.0 mL) in EtOH (100 mL) is added Fe (0.73 g, 13 mmol). The reaction mixture is heated at 50° C. for 16 hrs. Then the solid is filtered and the filtrate is concentrated. To the residue is added DCM and the mixture is filtered again and the filtrate is concentrated to give 0.25 g of 3-bromo-5-(3-methanesulfonyl-propoxy)-pyridine.

Workup

  1. filtrationThen the solid is filtered
  2. concentrationthe filtrate is concentrated
  3. additionTo the residue is added DCM
  4. filtrationthe mixture is filtered again
  5. concentrationthe filtrate is concentrated

Sources & evidence

ORD record
ord-8711c6ac69e24e359ed23a4b2ed0365d
Source dataset
uspto-grants-2015_11
Patent number
US09181272B2

Reaction notes

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