Nitric Acid → 6-Acetylamino-2-methyl-3-nitro-benzoic acid

HRID 343744

Reaction equation

HRID 343744 reaction equation
[N+:1]([O-:4])(O)=[O:2].[CH3:5][C:6]1[CH:14]=[CH:13][CH:12]=[C:11]([NH:15][C:16](=[O:18])[CH3:17])[C:7]=1[C:8]([OH:10])=[O:9]>O>[CH3:5][C:6]1[C:14]([N+:1]([O-:4])=[O:2])=[CH:13][CH:12]=[C:11]([NH:15][C:16](=[O:18])[CH3:17])[C:7]=1[C:8]([OH:10])=[O:9]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 28014002-Acetamido-6-methylbenzoic acid

Product 1

HCID 152831716-Acetylamino-2-methyl-3-nitro-benzoic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
10 °C

Procedure

271 ml of 98 percent nitric acid are initially taken at -5° C. and 106 g (0.55 mol) of the 2-methyl-6-acetamidobenzoic acid prepared in 1. are added in portions. After stirring at 10° C. for one hour, the reaction mixture is poured into a mixture of 540 g of ice and 270 ml of water. The deposited precipitate is filtered off with suction, washed with water and dried under reduced pressure at 50° C. Yield: 75.6 g (0.317 mol)=58% of theory, m.p.: 190°-191° C.

Workup

  1. customare initially taken at -5° C.
  2. additionare added in portions
  3. filtrationThe deposited precipitate is filtered off with suction
  4. washwashed with water
  5. customdried under reduced pressure at 50° C

Sources & evidence

ORD record
ord-de98427ec9a7475b89db67ef486e2342
Source dataset
uspto-grants-1999_01
Patent number
US05863864

Linked notes

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