Nitric Acid → Methyl 3-nitro-2-(pentanoylamino)benzoate

HRID 653700Notes

Reaction equation

HRID 653700 reaction equation
[N+:1]([O-:4])(O)=[O:2].S(=O)(=O)(O)O.[C:10]([NH:16][C:17]1[CH:26]=[CH:25][CH:24]=[CH:23][C:18]=1[C:19]([O:21][CH3:22])=[O:20])(=[O:15])[CH2:11][CH2:12][CH2:13][CH3:14]>C(OC(=O)C)(=O)C>[N+:1]([C:26]1[C:17]([NH:16][C:10](=[O:15])[CH2:11][CH2:12][CH2:13][CH3:14])=[C:18]([CH:23]=[CH:24][CH:25]=1)[C:19]([O:21][CH3:22])=[O:20])([O-:4])=[O:2]

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 1118Sulfuric AcidHCID 1734908HCID 1734908, compound

Product 1

HCID 15291136Methyl 3-nitro-2-(pentanoylamino)benzoateYield 28%

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Procedure

Fuming nitric acid (7.0 ml) was added dropwise to acetic anhydride (60 ml) under ice-cooling and there was added conc. sulfuric acid (0.2 ml). To the mixture was added methyl 2-valerylaminobenzoate (12 g), which was stirred for one hour at room temperature. To the resultant mixture was added ice-water and the mixture was then extracted with ethyl acetate. The organic layer was washed with water, dried and concentrated. The concentrate was purified by column chromatography on silica gel to give crude crystals, followed by recrystallization from isopropyl ether to afford colorless needles (3.9 g, 28%), m.p. 61°-62° C.

Workup

  1. temperaturecooling
  2. extractionthe mixture was then extracted with ethyl acetate
  3. washThe organic layer was washed with water
  4. customdried
  5. concentrationconcentrated
  6. customThe concentrate was purified by column chromatography on silica gel
  7. customto give crude crystals
  8. customfollowed by recrystallization from isopropyl ether

Sources & evidence

ORD record
ord-b087ec44fb814499a888b022426caa50
Source dataset
uspto-grants-1992_07
Patent number
US05128356

Reaction notes

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