Hydrochloric Acid → 4,5-Diethyl 1-methyl-1H-pyrazole-4,5-dicarboxylate

HRID 2382723

반응식

HRID 2382723 반응식
[CH3:1][NH:2]N.Cl.[CH2:5]([O:7][C:8](=[O:21])[C:9](=[CH:17][N:18](C)C)[C:10](=O)[C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH3:6]>C(O)C>[CH2:14]([O:13][C:11]([C:10]1[N:2]([CH3:1])[N:18]=[CH:17][C:9]=1[C:8]([O:7][CH2:5][CH3:6])=[O:21])=[O:12])[CH3:15]

참가 물질

5

반응물 3

HCID 313Hydrochloric AcidHCID 6061MethylhydrazineHCID 72733183Diethyl 2-((dimethylamino)methylene)-3-oxosuccinate

생성물 1

HCID 670417284,5-Diethyl 1-methyl-1H-pyrazole-4,5-dicarboxylate수율 36%

시약·촉매·용매 1

HCID 702Ethanol용매

반응 조건

온도
60 °C

실험 절차

Under an atmosphere of argon, methylhydrazine (1.15 g, 25 mmol) and HCl (36.5% in water, 2.5 ml) were added to a solution of 2-dimethylaminomethylene-3-oxo-succinic acid diethyl ester (6.07 g, 25 mmol, obtained by the method of Hanzlowsky et al., J. Heterocyclic Chem. 2003, 40(3), 487-498) in ethanol (200 ml). The mixture was heated to 60° C. until HPLC analysis indicated the disappearance of the starting material (2 h). The solvent was evaporated, and the residue was taken up in dichloromethane and washed (water). The organic layer was dried (Na2SO4), the solvent was evaporated and the title compound (2.06 mg, 36%) was isolated from the mixture by column chromatography (silica gel, heptane:ethyl acetate=100:0-60:40). (The regioisomeric 1-methyl-1H-pyrazole-3,4-dicarboxylic acid diethyl ester can also be isolated, and can be distinguished from the desired product by NOE-1H-NMR.) MS (m/e)=227.2 [M+H+].

후처리

  1. customobtained by the method of Hanzlowsky et al., J
  2. customthe disappearance of the starting material (2 h)
  3. customThe solvent was evaporated
  4. washwashed (water)
  5. dry with materialThe organic layer was dried (Na2SO4)
  6. customthe solvent was evaporated

출처 및 근거

ORD 기록
ord-0269e6d90c5045898f6616a901b0d342
출처 데이터셋
uspto-grants-2012_09
특허 번호
US08263584B2

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