Triethylamine → HCID 70665405, compound

HRID 333542Notes

Reaction equation

HRID 333542 reaction equation
Cl[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=1.[CH:11]1[C:19]2[C:18]3[CH:20]=[CH:21][CH:22]=[CH:23][C:17]=3[O:16][C:15]=2[C:14]([NH2:24])=[CH:13][CH:12]=1.C(N(CC)CC)C>C(O)CCC>[CH:11]1[C:19]2[C:18]3[CH:20]=[CH:21][CH:22]=[CH:23][C:17]=3[O:16][C:15]=2[C:14]([NH:24][C:2]2[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=2)=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 796132-Chloro-3-nitropyridineHCID 4593514-Dibenzofuranamine

Product 1

HCID 70665405HCID 70665405, compound

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

2-chloro-3-nitropyridine (4.39 g, 27.7 mmol), dibenzo[b,d]furan-4-amine (5.58 g, 30.5 mmol), triethylamine (4.3 mL, 30.9 mmol), and butanol (90 mL) were mixed in a 250 mL round bottom flask. The reaction mixture was refluxed overnight under nitrogen. The solvent was evaporated, leaving an orange solid which was dried under vacuum. The solid was taken up in ethyl acetate, water was added and the layers were separated. The organic layer with washed with brine, dried over magnesium sulfate, filtered, and evaporated to a residue. The residue was purified on by column chromatography eluting with 10% ethyl acetate/hexanes followed by ethyl acetate (4.6 g, 54%).

Workup

  1. temperatureThe reaction mixture was refluxed overnight under nitrogen
  2. customThe solvent was evaporated
  3. customleaving an orange solid which
  4. customwas dried under vacuum
  5. additionwater was added
  6. customthe layers were separated
  7. washThe organic layer with washed with brine
  8. dry with materialdried over magnesium sulfate
  9. filtrationfiltered
  10. customevaporated to a residue
  11. customThe residue was purified on by column chromatography
  12. washeluting with 10% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-78478ba2e325449491610abf7ec88fa0
Source dataset
uspto-grants-2014_11
Patent number
US08883322B2

Reaction notes

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