Triethylamine → HCID 22724299, compound

HRID 333546Notes

Reaction equation

HRID 333546 reaction equation
[C:1]1([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[C:3]([NH2:7])[CH:2]=1.Cl[C:15]1[C:20]([N+:21]([O-:23])=[O:22])=[CH:19][CH:18]=[CH:17][N:16]=1.C(N(CC)CC)C>C(O)CCC>[C:1]1([C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:6]=[CH:5][CH:4]=[C:3]([NH:7][C:15]2[C:20]([N+:21]([O-:23])=[O:22])=[CH:19][CH:18]=[CH:17][N:16]=2)[CH:2]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 167173-AminobiphenylHCID 796132-Chloro-3-nitropyridine

Product 1

HCID 22724299HCID 22724299, compound

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

[1,1′-biphenyl]-3-amine (8.49 g, 50.2 mmol), 2-chloro-3-nitropyridine (7.23 g, 45.6 mmol), triethylamine (6.99 mL, 50.2 mmol), and 200 mL of butanol were added to a 1 L round bottom flask. The mixture was refluxed overnight under nitrogen. The next day the solvent was evaporated, and the residue was taken up in dichloromethane and washed twice with water. The organic layer was dried over magnesium sulfate, filtered, and evaporated leaving an orange oil. 14.61 g, assume quantitative yield (13.29 g).

Workup

  1. temperatureThe mixture was refluxed overnight under nitrogen
  2. customThe next day the solvent was evaporated
  3. washwashed twice with water
  4. dry with materialThe organic layer was dried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customleaving an orange oil

Sources & evidence

ORD record
ord-e0c95ed71e264ef1a557fe8195b49728
Source dataset
uspto-grants-2014_11
Patent number
US08883322B2

Reaction notes

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