2-Aminobiphenyl → 2-Acetamidobiphenyl

HRID 1518629Notes

Reaction equation

HRID 1518629 reaction equation
[C:1]1([C:7]2[CH:13]=[CH:12][CH:11]=[CH:10][C:8]=2[NH2:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:14](OC(=O)C)(=[O:16])[CH3:15]>C(O)(=O)C>[C:1]1([C:7]2[CH:13]=[CH:12][CH:11]=[CH:10][C:8]=2[NH:9][C:14](=[O:16])[CH3:15])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 70152-AminobiphenylHCID 7918Acetic Anhydride

Product 1

HCID 164472-AcetamidobiphenylYield 99.5%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

2-Phenylaniline (5 g, 29.55 mmol) was dissolved in acetic acid (30 mL), acetic anhydride (3.62 g, 35.45 mmol) was added thereto under ice bath, and the mixture was stirred under ice bath for 2 hours. The solution was concentrated under reduced pressure. to the residue was added water (15 mL), and the mixture was stirred at room temperature for 3 hours. The precipitate was collected by filtration, washed with purified water, and dried under reduced pressure to obtain 2-phenyl-N-acetylaniline (6.21 g).

Workup

  1. concentrationThe solution was concentrated under reduced pressure
  2. additionto the residue was added water (15 mL)
  3. stirringthe mixture was stirred at room temperature for 3 hours
  4. filtrationThe precipitate was collected by filtration
  5. washwashed with purified water
  6. customdried under reduced pressure

Sources & evidence

ORD record
ord-ff96e38209dc4889b9b2b3a22262ad75
Source dataset
uspto-grants-2015_07
Patent number
US09072734B2

Reaction notes

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