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

HRID 1244255

反応式

HRID 1244255 の反応式
[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]

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
0 °C

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-368648d478334543afe2f74ff5c032db
出典データセット
uspto-grants-2006_10
特許番号
US07122546B2

関連ノート

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