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

HRID 585363

反応式

HRID 585363 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-3cc5cfec28264839b428a7fea88b71be
出典データセット
uspto-grants-2005_08
特許番号
US06930104B2

関連ノート

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