2-Aminobiphenyl → HCID 12545264, compound

HRID 383213Notes

Reaction equation

HRID 383213 reaction equation
F[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N+:8]([O-:10])=[O:9].[NH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.[F-].[K+]>>[N+:8]([C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[NH:11][C:12]1[C:13]([C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)=[CH:14][CH:15]=[CH:16][CH:17]=1)([O-:10])=[O:9]

Participants

4

Reactant 3

HCID 70152-AminobiphenylHCID 738951-Fluoro-2-nitrobenzeneHCID 522689Potassium Fluoride

Product 1

HCID 12545264HCID 12545264, compoundYield 91.1%

Conditions

Temperature
200 °C

Procedure

A mixture of 1-fluoro-2-nitrobenzene (13.06 g, 92.6 mmol), 2-aminobiphenyl (31.3 g, 185.2 mmol), and potassium fluoride (8.1 g, 138.9 mmol) was prepared in a 100 mL round bottom flask. The flask was evacuated and replaced with nitrogen. The mixture was heated to 200° C. overnight. The reaction mixture was cooled and ethyl acetate and water were added. The layers were separated and the aqueous layer was extracted with ethyl acetate. The organic layers were dried over magnesium sulfate, filtered, and evaporated. The residue was preabsorbed onto Celite and purified by column chromatography eluting with 0, 2, and 5% ethyl acetate/hexanes. 24.5 g (91%) of product was obtained.

Workup

  1. customwas prepared in a 100 mL round bottom flask
  2. customThe flask was evacuated
  3. temperatureThe reaction mixture was cooled
  4. additionethyl acetate and water were added
  5. customThe layers were separated
  6. extractionthe aqueous layer was extracted with ethyl acetate
  7. dry with materialThe organic layers were dried over magnesium sulfate
  8. filtrationfiltered
  9. customevaporated
  10. customThe residue was preabsorbed onto Celite
  11. custompurified by column chromatography
  12. washeluting with 0, 2, and 5% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-8b5b36b35f764088929926de479edb52
Source dataset
uspto-grants-2013_02
Patent number
US08367223B2

Reaction notes

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