Ammonium Chloride → HCID 11638090, compound

HRID 1982894Notes

Reaction equation

HRID 1982894 reaction equation
[F:1][C:2]1[CH:18]=[CH:17][C:5]([CH2:6][O:7][C:8]2[CH:9]=[N:10][CH:11]=[CH:12][C:13]=2[N+:14]([O-])=O)=[CH:4][CH:3]=1.[CH3:19][C:20]([Mg]Br)=[CH:21][CH3:22].[Cl-:25].[NH4+]>O1CCCC1>[ClH:25].[F:1][C:2]1[CH:18]=[CH:17][C:5]([CH2:6][O:7][C:8]2[C:13]3[NH:14][C:21]([CH3:22])=[C:20]([CH3:19])[C:12]=3[CH:11]=[N:10][CH:9]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 675283513-[(4-Fluorophenyl)methoxy]-4-nitropyridineHCID 178448414HCID 178448414, compound

Product 1

HCID 11638090HCID 11638090, compoundYield 13.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-20 °C

Procedure

3-(4-Fluorobenzyloxy)-4-nitropyridine (6.6 g, 26.59 mmol) prepared in Preparation 1 was dissolved in anhydrous tetrahydrofuran (300 ml) under a nitrogen atmosphere. 1-Methyl-1-propenyl magnesium bromide (0.5M in tetrahydrofuran solution, 80 ml) was added at −78° C. to the solution, which was then stirred for 5 hours at −20° C. 20 ml of 20% ammonium chloride solution was added to the reaction mixture, which was then extracted with ethyl acetate (200 ml) twice. The separated organic layer was dried on anhydrous magnesium sulfate and concentrated under reduced pressure. The resulting residue was purified with silica gel column chromatography (ethyl acetate/methanol=10/1 (v/v)) and then concentrated to remove the solvent. The resulting residue was dissolved in 10 ml of ethyl acetate and saturated with hydrochloric acid gas. The resulting precipitate was filtered to give the titled compound as a white solid (910 mg, 13.5%).

Workup

  1. extractionwas then extracted with ethyl acetate (200 ml) twice
  2. dry with materialThe separated organic layer was dried on anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe resulting residue was purified with silica gel column chromatography (ethyl acetate/methanol=10/1 (v/v))
  5. concentrationconcentrated
  6. customto remove the solvent
  7. dissolutionThe resulting residue was dissolved in 10 ml of ethyl acetate and saturated with hydrochloric acid gas
  8. filtrationThe resulting precipitate was filtered

Sources & evidence

ORD record
ord-d341459a7c9640a5b0774c9b73e7ed3a
Source dataset
uspto-grants-2009_06
Patent number
US07541366B2

Reaction notes

Loading…