Water → N-(2-Methoxy-6-nitrophenyl)valeroamide

HRID 1655468

반응식

HRID 1655468 반응식
[CH3:1][O:2][C:3]1[CH:9]=[CH:8][CH:7]=[C:6]([N+:10]([O-:12])=[O:11])[C:4]=1[NH2:5].S(=O)(=O)(O)O.[OH2:18].[OH-].[Na+]>C(OC(=O)CCCC)(=O)CCCC>[CH3:1][O:2][C:3]1[CH:9]=[CH:8][CH:7]=[C:6]([N+:10]([O-:12])=[O:11])[C:4]=1[NH:5][C:6](=[O:18])[CH2:4][CH2:3][CH2:9][CH3:8]

참가 물질

6

반응물 4

HCID 962WaterHCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 854916-Nitro-o-anisidine

생성물 1

HCID 19792196N-(2-Methoxy-6-nitrophenyl)valeroamide수율 36%

시약·촉매·용매 1

HCID 74959Valeric anhydride용매

반응 조건

온도
135 °C

실험 절차

To a mixture of 2-methoxy-6-nitroaniline (5.9 g) in valeric anhydride (14 g) was added a catalytic amount of conc. sulfuric acid, which was stirred for 1.5 hour at 130-140° C. To the reaction mixture was added water, which was made basic with 6N NaOH. The reaction mixture was extracted with ethyl acetate. The organic layer was washed with water and dried. The solvent was distilled off. The residue was purified by column chromatography on silica gel. Crude crystals thus obtained were recrystallized from ethyl acetate-hexane to give colorless crystals (3.2 g, 36%), m.p. 113-114° C.

후처리

  1. extractionThe reaction mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with water
  3. customdried
  4. distillationThe solvent was distilled off
  5. customThe residue was purified by column chromatography on silica gel
  6. customCrude crystals thus obtained
  7. customwere recrystallized from ethyl acetate-hexane

출처 및 근거

ORD 기록
ord-f84da17371ff45758fada74d8c615686
출처 데이터셋
uspto-grants-1993_10
특허 번호
US05250554

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