4-Chloroaniline → HCID 90387867, compound

HRID 874456Notes

Reaction equation

HRID 874456 reaction equation
[Br:1][C:2]1[C:3](Cl)=[N:4][CH:5]=[C:6]([N+:8]([O-:10])=[O:9])[CH:7]=1.[Cl:12][C:13]1[CH:19]=[CH:18][C:16]([NH2:17])=[CH:15][CH:14]=1>CS(C)=O>[Br:1][C:2]1[C:3]([NH:17][C:16]2[CH:18]=[CH:19][C:13]([Cl:12])=[CH:14][CH:15]=2)=[N:4][CH:5]=[C:6]([N+:8]([O-:10])=[O:9])[CH:7]=1

Participants

4

Reactant 2

HCID 78124-ChloroanilineHCID 2308893-Bromo-2-chloro-5-nitropyridine

Product 1

HCID 90387867HCID 90387867, compoundYield 68.5%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 3-bromo-2-chloro-5-nitropyridine (2.374 g, 10 mmol) and 4-chloroaniline (2.55 g, 20.00 mmol) in dimethylsulfoxide (20 mL) was heated at 90° C. for 2 hours. After cooling to ambient temperature, the reaction mixture was partitioned between water and ethyl acetate. The organic layer was separated, and the aqueous layer was extracted with additional ethyl acetate twice. The combined organic layers were washed with saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate, filtered, and concentrated. The residue was purified on silica gel eluting with 1:20 ethyl acetate/heptanes to give the crude product. This material was then triturated with 10% ethyl acetate in heptanes to give title compound (2.25 g, 6.85 mmol, 68.5% yield).

Workup

  1. temperatureAfter cooling to ambient temperature
  2. customthe reaction mixture was partitioned between water and ethyl acetate
  3. customThe organic layer was separated
  4. extractionthe aqueous layer was extracted with additional ethyl acetate twice
  5. washThe combined organic layers were washed with saturated aqueous sodium chloride
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe residue was purified on silica gel eluting with 1:20 ethyl acetate/heptanes
  10. customto give the crude product
  11. customThis material was then triturated with 10% ethyl acetate in heptanes

Sources & evidence

ORD record
ord-c9775018af2d41d5b9990bfc71e57487
Source dataset
uspto-grants-2015_03
Patent number
US08980879B2

Reaction notes

Loading…