N-Acetyl-4-aminobiphenyl → Acetamide, N-(3-nitro(1,1'-biphenyl)-4-yl)-

HRID 742334

Reaction equation

HRID 742334 reaction equation
[NH:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:7][CH:6]=1)[C:2]([CH3:4])=[O:3].[N+:17]([O-])([O-:19])=[O:18].[K+]>C(O)(=O)C.S(=O)(=O)(O)O>[NH:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:7][C:6]=1[N+:17]([O-:19])=[O:18])[C:2]([CH3:4])=[O:3]

Participants

5

Reactant 2

HCID 19998N-Acetyl-4-aminobiphenylHCID 24434Potassium Nitrate

Product 1

HCID 79364Acetamide, N-(3-nitro(1,1'-biphenyl)-4-yl)-Yield 42.1%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 1118Sulfuric AcidSolvent

Procedure

4-Acetaminobiphenyl (17 g, 80.57 mmol)in glacial acetic acid (600 ml) was added a solution of potassium nitrate (18 g, 178 mmol) in conc. sulphuric acid (75 ml) at such a rate that the temperature was kept below 30° C. Following the addition the mixture was stirred at ambient temperature for 72 hours. The reaction mixture was poured into ice-water (1200 ml). The product was filtered off, washed thoroughly with water and dried. Recrystallization from EtOH (99%, 150 ml) afforded 4-acetamino-3-nitrobiphenyl (8.7 g).

Workup

  1. customwas kept below 30° C
  2. additionthe addition the mixture
  3. filtrationThe product was filtered off
  4. washwashed thoroughly with water
  5. customdried
  6. customRecrystallization from EtOH (99%, 150 ml)

Sources & evidence

ORD record
ord-ef4eecd944054dbb9b866479b57c88ed
Source dataset
uspto-grants-1996_09
Patent number
US05554630

Linked notes

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