Nitric Acid → 4-Acetamido-3-nitrobenzophenone

HRID 1855818Notes

Reaction equation

[C:1]([NH:4][C:5]1[CH:18]=[CH:17][C:8]([C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:10])=[CH:7][CH:6]=1)(=[O:3])[CH3:2].C(OC(=O)C)(=O)C.[N+:26]([O-])([OH:28])=[O:27].NC(N)=O.C(C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(O)(=O)C>[C:1]([NH:4][C:5]1[CH:18]=[CH:17][C:8]([C:9]([C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)=[O:10])=[CH:7][C:6]=1[N+:26]([O-:28])=[O:27])(=[O:3])[CH3:2]

Participants

Conditions

Temperature: 50 °C

Procedure

Twenty-three grams (0.1 m.) of 4-acetamidobenzophenone, 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

additionThe thick slurry was poured over ice
filtrationthe insoluble product was filtered
customto yield 17.7 g

Sources & evidence

ORD record: ord-9c3e492aefe748dc95c44552f56228fc
Source dataset: uspto-grants-1980_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04216313

Reaction notes

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