Nitric Acid → 3-Acetamido-4-methyl-2-nitrobenzoic acid

HRID 1668918

Reaction equation

HRID 1668918 reaction equation
[C:1]([NH:4][C:5]1[CH:6]=[C:7]([CH:11]=[CH:12][C:13]=1[CH3:14])[C:8]([OH:10])=[O:9])(=[O:3])[CH3:2].[N+:15]([O-])([OH:17])=[O:16]>>[C:1]([NH:4][C:5]1[C:6]([N+:15]([O-:17])=[O:16])=[C:7]([CH:11]=[CH:12][C:13]=1[CH3:14])[C:8]([OH:10])=[O:9])(=[O:3])[CH3:2]

Participants

3

Reactant 2

HCID 944Nitric AcidHCID 2434323-Acetamido-4-methylbenzoic acid

Product 1

HCID 2434333-Acetamido-4-methyl-2-nitrobenzoic acidYield 63%

Procedure

3-Acetamido-4-methylbenzoic acid (205 g, 1061 mmol) was added portionwise over 45 min to stirred fuming nitric acid (1 L) at −5° C., maintaining a reaction temperature below 0° C. The mixture was stirred for an additional 1 h and then crushed ice (2.5 kg) was added. The mixture was stirred for a further 30 min. The precipite that formed was filtered off and thoroughly washed with water. The resulting cake was air dried and suspended in 1 L of acetic acid at 65° C. The suspension was stirred for 1 hour, allowed to cool down to RT and then filtered. The filtrate was washed with acetic acid and ether to give 3-acetamido-4-methyl-2-nitrobenzoic acid (160 g, 63%) as a white solid. MS (M+H)+ 239.

Workup

  1. temperaturemaintaining a reaction temperature below 0° C
  2. stirringThe mixture was stirred for a further 30 min
  3. customThe precipite that formed
  4. filtrationwas filtered off
  5. washthoroughly washed with water
  6. customdried
  7. customsuspended in 1 L of acetic acid at 65° C
  8. stirringThe suspension was stirred for 1 hour
  9. filtrationfiltered
  10. washThe filtrate was washed with acetic acid and ether

Sources & evidence

ORD record
ord-211ad1ef95614473accc3acc8d2750c0
Source dataset
uspto-grants-2011_08
Patent number
US07989461B2

Linked notes

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