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

HRID 872241노트

반응식

HRID 872241 반응식
[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]

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 23994Zinc촉매HCID 312751,4-Dioxane용매

실험 절차

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, 1 H), 9.15 (d, J=2.0, 1 H), 7.72 (s, 1 H), 4.51 (q, J=7.2, 2 H), 4.18 (s, 3 H), 1.47 (t, J=7.2, 3 H).

후처리

  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)

출처 및 근거

ORD 기록
ord-59eea77a77e44de7969cf6827d6f3d4d
출처 데이터셋
uspto-grants-2015_03
특허 번호
US08975278B2

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