Nitric Acid → 2-acetamido-3-methyl-5-nitrobenzoic acid

HRID 251991Notes

Reaction equation

HRID 251991 reaction equation
[C:1]([NH:4][C:5]1[C:13]([CH3:14])=[CH:12][CH:11]=[CH:10][C:6]=1[C:7]([OH:9])=[O:8])(=[O:3])[CH3:2].S(=O)(=O)(O)O.[N+:20]([O-])([OH:22])=[O:21]>>[C:1]([NH:4][C:5]1[C:13]([CH3:14])=[CH:12][C:11]([N+:20]([O-:22])=[O:21])=[CH:10][C:6]=1[C:7]([OH:9])=[O:8])(=[O:3])[CH3:2]

Participants

4

Reactant 3

HCID 944Nitric AcidHCID 1118Sulfuric AcidHCID 126392042-Acetamido-3-methylbenzoic acid

Product 1

HCID 40267322-acetamido-3-methyl-5-nitrobenzoic acidYield 50.7%

Procedure

To a mixture of 0.72 g of 2-acetylamino-3-methylbenzoic acid and 8 ml of concentrated sulfuric acid was added dropwise 1.6 g of fuming nitric acid at room temperature. The resulting mixture was stirred at room temperature for 2 hours. The reaction mixture was poured into ice water. A deposited precipitate was collected by filtration to obtain 0.45 g of 2-acetylamino-3-methyl-5-nitrobenzoic acid of the formula:

Workup

  1. filtrationA deposited precipitate was collected by filtration

Sources & evidence

ORD record
ord-31aca66e52e04c788cf2254702deb046
Source dataset
uspto-grants-2011_01
Patent number
US07867949B2

Reaction notes

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