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

HRID 1655463노트

반응식

HRID 1655463 반응식
[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]

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 7918Acetic Anhydride용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-b756d71df9b141eba7dc4bc540c3cef3
출처 데이터셋
uspto-grants-1993_10
특허 번호
US05250554

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