Nitric Acid → 4-Acetamido-3-nitrobenzoic acid

HRID 2260098Notes

Reaction equation

HRID 2260098 reaction equation
[C:1]([NH:4][C:5]1[CH:13]=[CH:12][C:8]([C:9]([OH:11])=[O:10])=[CH:7][CH:6]=1)(=[O:3])[CH3:2].[N+:14]([O-])([OH:16])=[O:15]>>[N+:14]([C:6]1[CH:7]=[C:8]([CH:12]=[CH:13][C:5]=1[NH:4][C:1](=[O:3])[CH3:2])[C:9]([OH:11])=[O:10])([O-:16])=[O:15]

Participants

3

Reactant 2

HCID 944Nitric AcidHCID 19266p-Acetamidobenzoic acid

Product 1

HCID 737584-Acetamido-3-nitrobenzoic acid

Procedure

In this reaction sequence, partially described by Kumar et al., J. Med. Chem., 27, pp. 1083-1089 (1984), 4-acetamidobenzoic acid is utilized as a starting material and is nitrated using, for instance, fuming nitric acid at about -10° to about 10° C. for 1-4 hours to afford 3-nitro-4-acetamidobenzoic acid. This compound is then reacted with thionyl chloride in a non-polar, aprotic solvent to afford the corresponding 3-nitro-4-acetamidobenzoyl chloride, which is then further reacted with the R'1 --H amine wherein R'1 is an amino group or a --NR4R5 group, to afford the 3-nitro-4-acetamino compound of formula V.

Workup

  1. customat about -10° to about 10° C.
  2. customfor 1-4 hours

Sources & evidence

ORD record
ord-098c92c108ca401dad6d8f53c86ce747
Source dataset
uspto-grants-1995_12
Patent number
US05476849

Reaction notes

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