Nitrobenzene → HCID 18005067, compound

HRID 1977748Notes

Reaction equation

HRID 1977748 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][CH:8]=[CH:7]2)([O-:3])=[O:2].Br[C:14]1[CH:15]=[N:16][CH:17]=[CH:18][CH:19]=1.C(=O)([O-])[O-].[K+].[K+].[N+](C1C=CC=CC=1)([O-])=O>N1C=CC=CC=1.O.[Cu]Br>[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[N:9]([C:14]1[CH:15]=[N:16][CH:17]=[CH:18][CH:19]=1)[CH:8]=[CH:7]2)([O-:3])=[O:2]

Participants

8

Reactant 4

HCID 7416NitrobenzeneHCID 11430Potassium CarbonateHCID 122863-BromopyridineHCID 225235-Nitroindole

Product 1

HCID 18005067HCID 18005067, compoundYield 86.5%

Reagents, catalysts & solvents 3

HCID 24593copper(I) bromideCatalystHCID 962WaterSolventHCID 1049PyridineSolvent

Procedure

A mixture of 5-nitroindole (0.49 g, 3 mmol), 3-bromopyridine (0.95 g, 6 mmol), copper (I) bromide (60 mg, 0.42 mmol) and potassium carbonate (0.62 g, 4.5 mmol) in pyridine (2 (mL) and nitrobenzene (0.6 mL) was heated under reflux for 4 h. After cooling, the mixture was diluted with water and extracted wtih ethyl acetate. The organic extract was washed with water, dried and evaporated. The residue was chromatographed on silica gel eluted with ethyl acetate to give the title compound (0.62 g, 86.5%), mp. 164-5° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 4 h
  3. temperatureAfter cooling
  4. extractionextracted wtih ethyl acetate
  5. extractionThe organic extract
  6. washwas washed with water
  7. customdried
  8. customevaporated
  9. customThe residue was chromatographed on silica gel
  10. washeluted with ethyl acetate

Sources & evidence

ORD record
ord-1f1c6a2a478642f89a9de9f52274e71a
Source dataset
uspto-grants-2001_05
Patent number
US06235758B1

Reaction notes

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