Nitric Acid → 2-Acetylamino-4-chloro-5-nitrobenzoic acid methyl ester

HRID 1858170Notes

Reaction equation

HRID 1858170 reaction equation
S(=O)(=O)(O)O.[N+:6]([O-:9])(O)=[O:7].[CH3:10][O:11][C:12](=[O:24])[C:13]1[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][C:14]=1[NH:20][C:21](=[O:23])[CH3:22]>>[CH3:10][O:11][C:12](=[O:24])[C:13]1[CH:18]=[C:17]([N+:6]([O-:9])=[O:7])[C:16]([Cl:19])=[CH:15][C:14]=1[NH:20][C:21](=[O:23])[CH3:22]

Participants

4

Reactant 3

HCID 944Nitric AcidHCID 1118Sulfuric AcidHCID 2800203Benzoic acid, 2-(acetylamino)-4-chloro-, methyl ester

Product 1

HCID 544712152-Acetylamino-4-chloro-5-nitrobenzoic acid methyl ester

Conditions

Temperature
0 °C

Procedure

To a solution of 3 mL conc. sulfuric acid and 0.40 mL of 90% nitric acid at 0° C. was added 2-acetylamino-4-chlorobenzoic acid methyl ester (1.5 g) in three portions over a period of 20 minutes. This was stirred at 0° C. for 30 minutes then allowed to warm to room temperature for an additional 1 hour. At this time the reaction was poured into 50 mL of an ice/water mixture and extracted with ethyl acetate (3×50 mL). The combined organics were washed sequentially with water (2×50 mL), 10% sodium bicarbonate (2×50 mL) and brine (50 mL) then dried over magnesium sulfate and concentrated in vacuo. Recrystallization of the crude product from methanol gave the title compound (1.02 g).

Workup

  1. temperatureto warm to room temperature for an additional 1 hour
  2. extractionextracted with ethyl acetate (3×50 mL)
  3. washThe combined organics were washed sequentially with water (2×50 mL), 10% sodium bicarbonate (2×50 mL) and brine (50 mL)
  4. dry with materialthen dried over magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customRecrystallization of the crude product from methanol

Sources & evidence

ORD record
ord-e82b8300d63b40639f290f6db5971fe4
Source dataset
uspto-grants-2000_11
Patent number
US06150522

Reaction notes

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