Acetic Acid → Ethyl 5,7-dichloro-8-methoxyquinoline-3-carboxylate

HRID 623417ノート

反応式

HRID 623417 の反応式
[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[N:8][C:9]2[C:14]([C:15]=1Cl)=[C:13]([Cl:17])[CH:12]=[C:11]([Cl:18])[C:10]=2[O:19][CH3:20])=[O:5])[CH3:2].C(O)(=O)C.C(OCC)(=O)C>O1CCOCC1.[Zn]>[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[N:8][C:9]2[C:14]([CH:15]=1)=[C:13]([Cl:17])[CH:12]=[C:11]([Cl:18])[C:10]=2[O:19][CH3:20])=[O:5])[CH3:2]

参加物

6

反応物 3

HCID 176Acetic AcidHCID 8857Ethyl AcetateHCID 57939336Ethyl 4,5,7-trichloro-8-methoxyquinoline-3-carboxylate

生成物 1

HCID 57939343Ethyl 5,7-dichloro-8-methoxyquinoline-3-carboxylate収率 39.7%

試薬・触媒・溶媒 2

HCID 23994Zinc触媒HCID 312751,4-Dioxane溶媒

実験手順

A suspension of zinc powder (0.70 g) was stirred at 20° C. in a solution of 4,5,7-trichloro-8-methoxy-quinoline-3-carboxylic acid ethyl ester 26 (364 mg, 1.09 mmol) and acetic acid (2.2 ml) in 1,4-dioxane (15 ml). After 20 minutes, ethyl acetate (20 ml) was added and the resultant mixture filtered through a pad of celite. The filtrate was washed with saturated aqueous sodium chloride solution (10 ml), dried (MgSO4), filtered, and the solvent removed under vacuum. The residue was chromatographed on flash silica (ethyl acetate/hexane, 1:9), yielding 130 mg (39%) of the title compound 27 as a white solid. 1H NMR (CDCl3, 400 MHz): δ 9.51 (d, J=2.0, 1H), 9.15 (d, J=2.0, 1H), 7.72 (s, 1H), 4.51 (q, J=7.2, 2 H), 4.18 (s, 3H), 1.47 (t, J=7.2, 3 H).

後処理

  1. filtrationthe resultant mixture filtered through a pad of celite
  2. washThe filtrate was washed with saturated aqueous sodium chloride solution (10 ml)
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. customthe solvent removed under vacuum
  6. customThe residue was chromatographed on flash silica (ethyl acetate/hexane, 1:9)

出典と根拠

ORDレコード
ord-74764e4943264b4eaf067337754ccfd8
出典データセット
uspto-grants-2016_04
特許番号
US09302993B2

反応ノート

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