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

HRID 1375288Notes

Reaction equation

HRID 1375288 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-3c2595b334c94e449c32a2887536c6ec
Source dataset
uspto-grants-2007_01
Patent number
US07166659B2

Reaction notes

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