Nitric Acid → 4-Acetamido-3-nitrobenzophenone

HRID 26377Notes

Reaction equation

HRID 26377 reaction equation
[C:1](OC(=O)C)(=O)C.[N+:8]([O-:11])(O)=[O:9].[NH2:12][C:13](N)=[O:14].[C:16]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)(=[O:23])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>C(O)(=O)C>[C:13]([NH:12][C:20]1[CH:21]=[CH:22][C:17]([C:16]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[O:23])=[CH:18][C:19]=1[N+:8]([O-:11])=[O:9])(=[O:14])[CH3:1]

Participants

6

Reactant 4

HCID 944Nitric AcidHCID 1176UreaHCID 3102BenzophenoneHCID 7918Acetic Anhydride

Product 1

HCID 5969694-Acetamido-3-nitrobenzophenoneYield 62.5%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Conditions

Temperature
50 °C

Procedure

Twenty-three grams (0.1 m.) of 4-acetamidonbenzophenone, 50 ml. of acetic anhydride and 20 ml. of acetic acid were stirred together. A solution of 90 percent nitric acid (15 ml.), 10 ml. of acetic acid and 0.2 g. of urea was added dropwise to the benzophenone mixture. The reaction mixture was maintained at a temperature of about 50° C. during the nitration. The mixture was stirred at ambient temperature whereupon the mixture became very thick. The thick slurry was poured over ice and the insoluble product was filtered to yield 17.7 g. (62.5 percent yield) of 4-acetamido-3-nitrobenzophenone.

Workup

  1. additionThe thick slurry was poured over ice
  2. filtrationthe insoluble product was filtered
  3. customto yield 17.7 g

Sources & evidence

ORD record
ord-20ce1551141f46029f3fc8dbcb037de1
Source dataset
uspto-grants-1979_04
Patent number
US04150028

Reaction notes

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