Hydrochloric Acid → Ethyl 2-{[4-(2-methoxyethoxy)-2-nitrophenyl]hydrazono}propanoate

HRID 504753노트

반응식

HRID 504753 반응식
[CH3:1][O:2][CH2:3][CH2:4][O:5][C:6]1[CH:12]=[CH:11][C:9]([NH2:10])=[C:8]([N+:13]([O-:15])=[O:14])[CH:7]=1.Cl.[N:17]([O-])=O.[Na+].[CH3:21][CH:22](C(C)=O)[C:23]([O:25][CH2:26][CH3:27])=[O:24].[OH-].[K+]>O.C(O)C.C(#N)C>[CH3:1][O:2][CH2:3][CH2:4][O:5][C:6]1[CH:12]=[CH:11][C:9]([NH:10][N:17]=[C:22]([CH3:21])[C:23]([O:25][CH2:26][CH3:27])=[O:24])=[C:8]([N+:13]([O-:15])=[O:14])[CH:7]=1

참가 물질

9

반응물 5

HCID 313Hydrochloric AcidHCID 701Ethyl 2-methylacetoacetateHCID 14797Potassium HydroxideHCID 204787644-(2-Methoxyethoxy)-2-nitroanilineHCID 23668193Sodium Nitrite

생성물 1

HCID 76540791Ethyl 2-{[4-(2-methoxyethoxy)-2-nitrophenyl]hydrazono}propanoate수율 6%

시약·촉매·용매 3

HCID 702Ethanol용매HCID 962Water용매2회HCID 6342Acetonitrile용매

반응 조건

온도
7.5 °C

실험 절차

To a mixture of 4-(2-methoxyethoxy)-2-nitroaniline (15.0 g), 6N hydrochloric acid (59 mL) and acetonitrile (50 mL) was added dropwise an aqueous solution (50 mL) of sodium nitrite (4.88 g) at 5-10° C. The reaction mixture was stirred at 5-10° C. for 1.5 hr. This mixture was added to a mixture of ethyl 2-methylacetoacetate (11.2 g), 85% potassium hydroxide (23.8 g), ethanol (50 mL) and water (50 mL) at 10-20° C. The reaction mixture was stirred at 10° C. for 10 min, water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, dried (MgSO4), and concentrated. The obtained residue was subjected to silica gel column chromatography, and eluted with hexane-ethyl acetate (4:1-2:1, volume ratio) to give the title compound (1.39 g, yield 6%) as orange crystals.

후처리

  1. stirringThe reaction mixture was stirred at 10° C. for 10 min
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe ethyl acetate layer was washed with saturated brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated
  6. washeluted with hexane-ethyl acetate (4:1-2:1, volume ratio)

출처 및 근거

ORD 기록
ord-74f9ee2661864c2f8250798a005118ad
출처 데이터셋
uspto-grants-2010_08
특허 번호
US07777047B2

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