Nitric Acid → Methyl 5-methyl-3-nitro-2-valerylaminobenzoate

HRID 1655463Notes

Reaction equation

HRID 1655463 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([NH:12][C:13](=[O:18])[CH2:14][CH2:15][CH2:16][CH3:17])=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8].[N+:19]([O-])([OH:21])=[O:20]>C(OC(=O)C)(=O)C>[CH3:1][C:2]1[CH:3]=[C:4]([N+:19]([O-:21])=[O:20])[C:5]([NH:12][C:13](=[O:18])[CH2:14][CH2:15][CH2:16][CH3:17])=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 19792094Methyl 5-methyl-2-valerylaminobenzoate

Product 1

HCID 19792147Methyl 5-methyl-3-nitro-2-valerylaminobenzoateYield 60%

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Procedure

To a mixture of methyl 5-methyl-2-valerylaminobenzoate (12.8 g) in acetic anhydride (5.9 g) was added dropwise, while stirring under ice-cooling, fuming nitric acid (6.7 ml), followed by stirring for 3 hours. To the reaction mixture was added ice water, which was extracted with ethyl acetate. The extract was washed with an aqueous solution of sodium bicarbonate and water, which was then dried. The solvent was evaporated to dryness, and the residue was purified by column chromatography on silica gel. Crystals thus obtained were recrystallized from isopropyl ether gave colorless crystals (8.5 g, 60%), m.p. 59-60° C.

Workup

  1. additionwas added dropwise
  2. temperaturecooling
  3. stirringby stirring for 3 hours
  4. extractionwas extracted with ethyl acetate
  5. washThe extract was washed with an aqueous solution of sodium bicarbonate and water, which
  6. customwas then dried
  7. customThe solvent was evaporated to dryness
  8. customthe residue was purified by column chromatography on silica gel
  9. customCrystals thus obtained
  10. customwere recrystallized from isopropyl ether

Sources & evidence

ORD record
ord-b756d71df9b141eba7dc4bc540c3cef3
Source dataset
uspto-grants-1993_10
Patent number
US05250554

Reaction notes

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