Ammonium Chloride → HCID 178433481, compound

HRID 520262Notes

Reaction equation

HRID 520262 reaction equation
[Br:1][C:2]1[C:3]([O:12][C@H:13]2[CH2:18][CH2:17][C@H:16]([CH:19]([CH3:21])[CH3:20])[CH2:15][CH2:14]2)=[N:4][C:5]([CH3:11])=[C:6]([N+:8]([O-])=O)[CH:7]=1.[Cl-].[NH4+]>CCO.O.[Fe]>[Br:1][C:2]1[CH:7]=[C:6]([NH2:8])[C:5]([CH3:11])=[N:4][C:3]=1[O:12][C@H:13]1[CH2:14][CH2:15][C@H:16]([CH:19]([CH3:20])[CH3:21])[CH2:17][CH2:18]1

Participants

5

Reactant 2

HCID 25517Ammonium ChlorideHCID 178433483HCID 178433483, compound

Product 1

HCID 178433481HCID 178433481, compoundYield 100.5%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 19096565Water ethanolSolvent

Procedure

To a stirred solution of 3-bromo-2-(trans-4-isopropylcyclohexoxy)-6-methyl-5-nitro-pyridine (0.917 g, 2.00 mmol) in EtOH/H2O (24 mL/6 mL, 4/1 v/v), ammonium chloride (0.109 g, 2.00 mmol, 1.0 eq) and iron powder (0.452 g, 8.00 mmol, 4 eq) were added at room temperature under inert atmosphere (Ar). The reaction mixture was stirred under heating to reflux for 3 h. At this point in time, TLC indicated that the starting material was consumed. Therefore, the reaction mixture was allowed to reach room temperature and was filtered through a pad of celite. The filtrate was concentrated under reduced pressure and the residue partitioned between a 2 molar aqueous NaOH solution (20 mL) and ethyl acetate (30 mL). The phases were separated and the aqueous phase extracted with ethyl acetate (2×20 mL). The organic layer was washed with brine (40 mL), dried over anhydrous Na2SO4 and filtered. The solvent was removed in vacuo to afford the title compound (0.658 g, 100%) as an oil.

Workup

  1. temperatureunder heating
  2. temperatureto reflux for 3 h
  3. customwas consumed
  4. customto reach room temperature
  5. filtrationwas filtered through a pad of celite
  6. concentrationThe filtrate was concentrated under reduced pressure
  7. customthe residue partitioned between a 2 molar aqueous NaOH solution (20 mL) and ethyl acetate (30 mL)
  8. customThe phases were separated
  9. extractionthe aqueous phase extracted with ethyl acetate (2×20 mL)
  10. washThe organic layer was washed with brine (40 mL)
  11. dry with materialdried over anhydrous Na2SO4
  12. filtrationfiltered
  13. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-8cb7f76accaf4c8a8df1a99fe0624ac3
Source dataset
uspto-grants-2016_05
Patent number
US09326513B2

Reaction notes

Loading…