Nitric Acid → Methyl 4-nitro-3-valerylaminobenzoate

HRID 1655459Notes

Reaction equation

HRID 1655459 reaction equation
[C:1]([NH:7][C:8]1[CH:9]=[C:10]([CH:15]=[CH:16][CH:17]=1)[C:11]([O:13][CH3:14])=[O:12])(=[O:6])[CH2:2][CH2:3][CH2:4][CH3:5].[N+:18]([O-])([OH:20])=[O:19]>C(OC(=O)C)(=O)C.S(=O)(=O)(O)O>[N+:18]([C:17]1[CH:16]=[CH:15][C:10]([C:11]([O:13][CH3:14])=[O:12])=[CH:9][C:8]=1[NH:7][C:1](=[O:6])[CH2:2][CH2:3][CH2:4][CH3:5])([O-:20])=[O:19]

Participants

5

Reactant 2

HCID 944Nitric AcidHCID 19171455Methyl 3-pentanamidobenzoate

Product 1

HCID 19792184Methyl 4-nitro-3-valerylaminobenzoateYield 36%

Reagents, catalysts & solvents 2

HCID 1118Sulfuric AcidCatalystHCID 7918Acetic AnhydrideSolvent

Procedure

To a solution of methyl 3-valerylaminobenzoate (2.3 g) in acetic anhydride (12 ml) was added dropwise fuming nitric acid (1.4 ml) while stirring under ice-cooling. To the mixture was added one drop of conc. sulfuric acid and the mixture was stirred for two hours. To the reaction mixture was added ice-water and it was extracted with ethyl acetate. The organic layer was washed with an aqueous solution of sodium bicarbonate and water and then dried. The solvent was evaporated to dryness, and the residue was purified by column chromatography on silica gel to afford a brown oil (1.0 g, 36%).

Workup

  1. temperaturecooling
  2. stirringthe mixture was stirred for two hours
  3. extractionwas extracted with ethyl acetate
  4. washThe organic layer was washed with an aqueous solution of sodium bicarbonate and water
  5. customdried
  6. customThe solvent was evaporated to dryness
  7. customthe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-145902ef52d14e1fb265a43d938ed10f
Source dataset
uspto-grants-1993_10
Patent number
US05250554

Reaction notes

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