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

HRID 1672476Notes

Reaction equation

HRID 1672476 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 Acid2×HCID 2434323-Acetamido-4-methylbenzoic acid

Product 1

HCID 2434333-Acetamido-4-methyl-2-nitrobenzoic acidYield 51.8%

Procedure

3-(acetylamino)-4-methylbenzoic acid (300 g, 1.55 mol) was added portionwise to fuming nitric acid (1200 mL) with stirring over a period of 1 h at 0˜5° C. The solution gradually turned into a heavy slurry during the addition. At the end of addition, an additional fuming nitric acid (200 mL) was added. The reaction mixture was stirred for an additional hour at 5° C., then allowed to warm to room temperature and poured into ice water. The solid formed was collected and washed with water (450 mL×3). The crude product was re-crystallized from acetic acid (1800 mL) to give the title compound (191.5 g, 51.8%) as a white solid.

Workup

  1. additionThe solution gradually turned into a heavy slurry during the addition
  2. additionAt the end of addition
  3. stirringThe reaction mixture was stirred for an additional hour at 5° C.
  4. customThe solid formed
  5. customwas collected
  6. washwashed with water (450 mL×3)
  7. customThe crude product was re-crystallized from acetic acid (1800 mL)

Sources & evidence

ORD record
ord-e033d4a997a044539dda701219f89826
Source dataset
uspto-grants-2011_08
Patent number
US07998978B2

Reaction notes

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