Acetic Acid → Methyl 2-acetamido-3-nitrobenzoate

HRID 1639830Notes

Reaction equation

HRID 1639830 reaction equation
[C:1]([O:10][CH3:11])(=[O:9])[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[NH2:4].[C:12]([OH:15])(=O)[CH3:13].[N+:16]([O-])([OH:18])=[O:17]>C(OC(=O)C)(=O)C>[C:12]([NH:4][C:3]1[C:5]([N+:16]([O-:18])=[O:17])=[CH:6][CH:7]=[CH:8][C:2]=1[C:1]([O:10][CH3:11])=[O:9])(=[O:15])[CH3:13]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 944Nitric AcidHCID 8635Methyl Anthranilate

Product 1

HCID 2782278Methyl 2-acetamido-3-nitrobenzoateYield 52%

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent2×

Conditions

Temperature
12.5 °C

Procedure

A solution of methyl anthranilate (21.0 mL, 162 mmol) in acetic anhydride (170 mL) was stirred at room temperature for 1 hr. To the reaction mixture was added dropwise a mixture of acetic anhydride (35 mL), acetic acid (30 mL) and 60% nitric acid (50 ml, 162 mmol) at 10-15° C. over 2 hr. The reaction mixture was stirred at 10-15° C. for 2.5 hr, and poured into ice-cold water. The resulting solid was collected by filtration, washed with water, and after recrystallization (chloroform/methanol), the crystals were collected by filtration. The filtrate was extracted with methylene chloride, and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was crystallized from ether to give the title compound (20.0 g, yield 52%).

Workup

  1. additionTo the reaction mixture was added dropwise
  2. additionpoured into ice-cold water
  3. filtrationThe resulting solid was collected by filtration
  4. washwashed with water
  5. customafter recrystallization (chloroform/methanol)
  6. filtrationthe crystals were collected by filtration
  7. extractionThe filtrate was extracted with methylene chloride
  8. dry with materialdried over anhydrous sodium sulfate
  9. customthe solvent was evaporated under reduced pressure
  10. customThe residue was crystallized from ether

Sources & evidence

ORD record
ord-4fac7d862ff1461285595959b0e60e75
Source dataset
uspto-grants-2012_02
Patent number
US08110585B2

Reaction notes

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