p-Fluoronitrobenzene → HCID 13580532, compound

HRID 1380543Notes

Reaction equation

HRID 1380543 reaction equation
[H-].[Na+].[CH3:3][C:4]1[C:5]([CH:10]([CH2:13][OH:14])[CH2:11][OH:12])=[N:6][CH:7]=[CH:8][CH:9]=1.F[C:16]1[CH:21]=[CH:20][C:19]([N+:22]([O-:24])=[O:23])=[CH:18][CH:17]=1>CN(C)C=O>[OH:12][CH2:11][CH:10]([C:5]1[C:4]([CH3:3])=[CH:9][CH:8]=[CH:7][N:6]=1)[CH2:13][O:14][C:16]1[CH:21]=[CH:20][C:19]([N+:22]([O-:24])=[O:23])=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 9590p-FluoronitrobenzeneHCID 24758Sodium hydrideHCID 14546503HCID 14546503, compound

Product 1

HCID 13580532HCID 13580532, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

60% Oil-borne sodium hydride (2.8 g) was added little by little to a solution of 2-(3-methyl-2-pyridyl)-1,3-propylene glycol (10.0 g) and p-fluoronitrobenzene (8.45 g) in dimethylformamide (100 ml) under ice-cooling with stirring. After stirring under ice-cooling for 1 hour, the reaction solution was poured in ice-cold water, and the aqueous mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with water, dried (MgSO4) and freed of the solvent by distillation, and the residue was chromatographed on a silica-gel (200 g) column. Elution was effected with cyclohexane-ethyl acetate (3:1, V/V) to give 4-[3-hydroxy-2-(3-methyl-2-pyridyl)propoxy]nitrobenzene in the form of crystals. Yield of 9.6 g. Recrystallization from ethyl acetatehexane produced colorless prisms. m.p. 135°-136° C.

Workup

  1. temperaturecooling
  2. stirringAfter stirring under ice-
  3. temperaturecooling for 1 hour
  4. additionthe reaction solution was poured in ice-cold water
  5. extractionthe aqueous mixture was extracted with ethyl acetate
  6. washThe ethyl acetate layer was washed with water
  7. dry with materialdried (MgSO4)
  8. distillationfreed of the solvent by distillation
  9. customthe residue was chromatographed on a silica-gel (200 g) column
  10. washElution

Sources & evidence

ORD record
ord-7dd1f63ac8f040df800de7a7f1c6836f
Source dataset
uspto-grants-1986_04
Patent number
US04582839

Reaction notes

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