Hydrochloric Acid → 6-Chloro-4-ethoxy-pyridazine-3-carboxylic acid ethyl ester

HRID 1244255

반응식

HRID 1244255 반응식
[O-:1][CH2:2][CH3:3].[Na+].[CH2:5]([O:7][C:8]([C:10]1[N:11]=[N:12][C:13]([Cl:17])=[CH:14][C:15]=1Cl)=[O:9])[CH3:6].Cl.C([O-])(O)=O.[Na+]>C1COCC1.CCOC(C)=O>[CH2:5]([O:7][C:8]([C:10]1[N:11]=[N:12][C:13]([Cl:17])=[CH:14][C:15]=1[O:1][CH2:2][CH3:3])=[O:9])[CH3:6]

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 2723922Sodium ethoxideHCID 53428795Ethyl 4,6-dichloropyridazine-3-carboxylate

생성물 1

HCID 859613046-Chloro-4-ethoxy-pyridazine-3-carboxylic acid ethyl ester

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

반응 조건

온도
0 °C

실험 절차

Sodium ethoxide (1.16 g, 17 mmol) is added to a stirred solution of 4,6-dichloropyridazine-3-carboxylic acid ethyl ester (3.73 g, 17 mmol) in THF (45 mL) cooled to 0° C. The reaction mixture is stirred at room temperature overnight and then poured into 1N HCl (20 mL). The resulting solution is then neutralized with saturated NaHCO3. EtOAc (20 mL) is added and the layers are separated. The aqueous layer is extracted twice with EtOAc (20 mL) and the combined extracts are washed with brine (25 mL), dried (Na2SO4), and evaporated. The residue is then purified by flash column chromatography (silica gel, eluted with 2:1 Hexane, EtOAc) to give the title product as a white solid. H1 NMR δ (CDCl3) 7.02 (s, 1H), 4.47 (q, 2H, J=7.2 Hz), 4.19 (q, 2H, J=7.2 Hz), 1.50 (t, 3H, J=7.2 Hz), 1.41 (t, 3H, J=7.2 Hz).

후처리

  1. customthe layers are separated
  2. extractionThe aqueous layer is extracted twice with EtOAc (20 mL)
  3. washthe combined extracts are washed with brine (25 mL)
  4. dry with materialdried (Na2SO4)
  5. customevaporated
  6. customThe residue is then purified by flash column chromatography (silica gel, eluted with 2:1 Hexane, EtOAc)

출처 및 근거

ORD 기록
ord-368648d478334543afe2f74ff5c032db
출처 데이터셋
uspto-grants-2006_10
특허 번호
US07122546B2

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