4-Hydroxybenzaldehyde → (2-Quinolinyl)-methoxyl-benzaldehyde

HRID 37697노트

반응식

HRID 37697 반응식
[Na].O[C:3]1[CH:10]=[CH:9][C:6]([CH:7]=[O:8])=[CH:5][CH:4]=1.ClC[C:13]1[CH:22]=[CH:21][C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[N:14]=1.Cl.[CH2:24]([OH:26])C>>[N:14]1[C:15]2[C:20](=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:21]=[CH:22][C:13]=1[C:4]1[C:5]([O:26][CH3:24])=[C:6]([CH:9]=[CH:10][CH:3]=1)[CH:7]=[O:8]

참가 물질

6

반응물 5

HCID 1264-HydroxybenzaldehydeHCID 313Hydrochloric AcidHCID 702Ethanol3회HCID 203942-(Chloromethyl)quinolineHCID 5360545Sodium

생성물 1

HCID 86748706(2-Quinolinyl)-methoxyl-benzaldehyde

실험 절차

To a solution of sodium metal (0.9 g, 39.13 g.a.) in absolute ethanol (50 mL) is added dropwise under nitrogen a solution of 4-hydroxybenzaldehyde (5 g, 40.94 mmole) in absolute ethanol (50 mL). The mixture is gently refluxed for 1 hour and then treated dropwise with a solution of 2-chloromethylquinoline (free base, 7.24 g, 40.76 mmole), freshly prepared from the HCl salt) in ethanol (50 mL). The mixture is refluxed for 24 hours, the solvent is evaporated and the residue is partitioned between water and ethyl acetate. The organic layer is washed with 5% NaOH (pH 8), water, brine to neutral and dried (MgSO4). Removal of the solvent yields the title compound as a yellow solid (9.81 g). The crude material is further purified by flash chromatography (on silica Merck-60, hexane-ethyl acetate 9:1 to remove less polar impurities and 8:2 to elute the product). Yield: 7.37 g (71.5%), m.p. 82°-83° C.

후처리

  1. temperatureThe mixture is gently refluxed for 1 hour
  2. temperatureThe mixture is refluxed for 24 hours
  3. customthe solvent is evaporated
  4. customthe residue is partitioned between water and ethyl acetate
  5. washThe organic layer is washed with 5% NaOH (pH 8), water, brine to neutral and
  6. dry with materialdried (MgSO4)
  7. customRemoval of the solvent

출처 및 근거

ORD 기록
ord-bd82b15bb44b4042a08c15a5a826b8bc
출처 데이터셋
uspto-grants-1995_05
특허 번호
US05420289

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