Nitric Acid → 4-Acetamido-3-methyl-5-nitrobenzoic acid

HRID 1177805Notes

Reaction equation

HRID 1177805 reaction equation
[N+:1]([O-:4])(O)=[O:2].[C:5]([NH:8][C:9]1[CH:17]=[CH:16][C:12]([C:13]([OH:15])=[O:14])=[CH:11][C:10]=1[CH3:18])(=[O:7])[CH3:6]>S(=O)(=O)(O)O>[C:5]([NH:8][C:9]1[C:17]([N+:1]([O-:4])=[O:2])=[CH:16][C:12]([C:13]([OH:15])=[O:14])=[CH:11][C:10]=1[CH3:18])(=[O:7])[CH3:6]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 30159484-(Acetylamino)-3-methylbenzoic acid

Product 1

HCID 210981464-Acetamido-3-methyl-5-nitrobenzoic acidYield 72%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 60% nitric acid in sulfuric acid (410 mL) was added 4-acetamido-3-methylbenzoic acid (43 g, 0.22 mol) in small portions over 40 min while cooling with an ice bath. After addition of all amide was complete, the reaction mixture was stirred for 1 h at 0° C. and then very slowly poured over 1500 mL of ice. The yellow solid was collected by filtration and washed with ice cold water to give the title compound (38 g, 72% yield). 1H-NMR (CD3OD, 300 MHz) δ 8.29 (s, 1H), 8.18 (s, 1H), 2.39 (s, 3H), 2.16 (s, 3H). Mass spec.: 237 (MH)+.

Workup

  1. temperaturewhile cooling with an ice bath
  2. filtrationThe yellow solid was collected by filtration
  3. washwashed with ice cold water

Sources & evidence

ORD record
ord-d77f6ba62c02453794ceeeb3bb040498
Source dataset
uspto-grants-2010_11
Patent number
US07842808B2

Reaction notes

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