Nitric Acid → Acetamide, N-(3-nitro(1,1'-biphenyl)-4-yl)-

HRID 1836061Notes

Reaction equation

HRID 1836061 reaction equation
[C:1]([NH:4][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)(=[O:3])[CH3:2].C(OC(=O)C)(=O)C.[N+:24]([O-])([OH:26])=[O:25]>O>[N+:24]([C:6]1[CH:7]=[C:8]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:9]=[CH:10][C:5]=1[NH:4][C:1](=[O:3])[CH3:2])([O-:26])=[O:25]

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 7918Acetic AnhydrideHCID 19998N-Acetyl-4-aminobiphenyl

Product 1

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

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of 4-acetamido-1,1′-biphenyl (21.1 g, 0.1 mol) and 150 mL of acetic anhydride maintained between 8° C. and 13° C. is slowly added dropwise over 32 minutes 12.7 mL of 70% nitric acid. The reaction mixture is added to 600 mL of a mixture of water and ice and the resultant precipitate is collected by filtration. The filter cake is washed with water and the residue is recrystallized from methanol (800 mL) to give 23.6 g of the title compound as a yellow crystalline solid melting at 129-132° C.

Workup

  1. temperaturemaintained between 8° C. and 13° C.
  2. filtrationthe resultant precipitate is collected by filtration
  3. washThe filter cake is washed with water
  4. customthe residue is recrystallized from methanol (800 mL)

Sources & evidence

ORD record
ord-06a4dcc1356e4ba9b4ef2276fb7bf6ef
Source dataset
uspto-grants-2004_08
Patent number
US06774238B2

Reaction notes

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