4-Ethoxy-m-anisic acid → 1-(4-Ethoxy-3-methoxybenzoyl)-2-methyl-1,2,3,4-tetrahydro-4-quinolinol

HRID 585363

반응식

HRID 585363 반응식
[CH3:1][CH:2]1[CH2:11][CH:10]([OH:12])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[NH:3]1.[CH2:13]([O:15][C:16]1[CH:24]=[CH:23][C:19]([C:20](Cl)=[O:21])=[CH:18][C:17]=1[O:25][CH3:26])[CH3:14].C(OC1C=CC(C(O)=O)=CC=1OC)C>N1C=CC=CC=1>[CH2:13]([O:15][C:16]1[CH:24]=[CH:23][C:19]([C:20]([N:3]2[C:4]3[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=3)[CH:10]([OH:12])[CH2:11][CH:2]2[CH3:1])=[O:21])=[CH:18][C:17]=1[O:25][CH3:26])[CH3:14]

참가 물질

5

반응물 3

HCID 770694-Ethoxy-m-anisic acidHCID 1476341,2,3,4-Tetrahydro-2-methyl-4-quinolinolHCID 128431534-Ethoxy-3-methoxybenzoyl chloride

생성물 1

HCID 223392011-(4-Ethoxy-3-methoxybenzoyl)-2-methyl-1,2,3,4-tetrahydro-4-quinolinol수율 30%

시약·촉매·용매 1

HCID 1049Pyridine용매

실험 절차

2-Methyl-1,2,3,4-tetrahydro-4-quinolinol (7.1 g, 43.5 mmol) synthesized in the published manner was dissolved in pyridine (50 ml), followed by addition of 4-ethoxy-3-methoxybenzoyl chloride prepared from 4-ethoxy-3-methoxybenzoic acid (9.2 g, 46.4 mmol). After stirring at room temperature for 16 hours, the reaction mixture was concentrated and extracted by addition of ethyl acetate and water. After the organic layer was dried and concentrated, the residue was applied to silica gel column chromatography (developing solvent: ethyl acetate/hexane=1/1) and the resulting eluate was recrystallized from ethyl acetate-hexane to give the titled compound (4.4 g, yield: 30%) as a white crystal.

후처리

  1. concentrationthe reaction mixture was concentrated
  2. extractionextracted by addition of ethyl acetate and water
  3. customAfter the organic layer was dried
  4. concentrationconcentrated
  5. customthe resulting eluate was recrystallized from ethyl acetate-hexane

출처 및 근거

ORD 기록
ord-3cc5cfec28264839b428a7fea88b71be
출처 데이터셋
uspto-grants-2005_08
특허 번호
US06930104B2

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