1-Chloro-4-nitrobenzene → HCID 19992431, compound

HRID 345439Notes

Reaction equation

HRID 345439 reaction equation
[H-].[Na+].[CH3:3][N:4]([CH2:11][CH2:12][OH:13])[C:5]1[CH:10]=[CH:9][N:8]=[CH:7][CH:6]=1.Cl[C:15]1[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][CH:16]=1>CN(C)C=O>[CH3:3][N:4]([C:5]1[CH:10]=[CH:9][N:8]=[CH:7][CH:6]=1)[CH2:11][CH2:12][O:13][C:15]1[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 74741-Chloro-4-nitrobenzeneHCID 24758Sodium hydrideHCID 10419367Ethanol, 2-(methyl-4-pyridinylamino)-

Product 1

HCID 19992431HCID 19992431, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (0.16 g of a 50% dispersion in mineral oil) was added portionwise to a stirred solution of the product of part (i) (0.45 g) in dry N,N-dimethylformamide (30 ml) and the mixture was stirred at 50° for 0.3 hour and then cooled to 5°. 4-Chloronitrobenzene (0.47 g) was added portionwise and the mixture was then stirred at room temperature for 2 hours and evaporated. Water was added and the mixture was extracted several times with dichloromethane. The combined extracts were dried (Na2SO4) and evaporated to give a yellow solid which was washed with hexane to remove mineral oil. The solid was chromatographed on silica gel using dichloromethane/methanol (10:1) as eluant. The product fractions were combined and evaporated to give pure product, (0.60 g), m.p. 88°-89° (from ethyl acetate/hexane).

Workup

  1. temperaturecooled to 5°
  2. stirringthe mixture was then stirred at room temperature for 2 hours
  3. customevaporated
  4. additionWater was added
  5. extractionthe mixture was extracted several times with dichloromethane
  6. dry with materialThe combined extracts were dried (Na2SO4)
  7. customevaporated
  8. customto give a yellow solid which
  9. washwas washed with hexane
  10. customto remove mineral oil
  11. customThe solid was chromatographed on silica gel
  12. customevaporated
  13. customto give pure product, (0.60 g), m.p. 88°-89° (from ethyl acetate/hexane)

Sources & evidence

ORD record
ord-20d321fc759d4502a75ad8d0c4b812c6
Source dataset
uspto-grants-1991_10
Patent number
US05057528

Reaction notes

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