4-Chlorobenzylamine → HCID 490481、化合物

HRID 1068051ノート

反応式

HRID 1068051 の反応式
[CH3:1][N:2]([CH3:22])[N:3]1[C:12]2[C:7](=[CH:8][C:9](I)=[CH:10][CH:11]=2)[C:6](=[O:14])[C:5]([C:15]([O:17]CCCC)=O)=[CH:4]1.[Cl:23][C:24]1[CH:31]=[CH:30][C:27]([CH2:28][NH2:29])=[CH:26][CH:25]=1>>[Cl:23][C:24]1[CH:31]=[CH:30][C:27]([CH2:28][NH:29][C:15]([C:5]2[C:6](=[O:14])[C:7]3[C:12](=[CH:11][CH:10]=[C:9]([C:4]#[C:5][CH2:6][OH:14])[CH:8]=3)[N:3]([N:2]([CH3:1])[CH3:22])[CH:4]=2)=[O:17])=[CH:26][CH:25]=1

参加物

3

反応物 2

HCID 660364-ChlorobenzylamineHCID 21192562HCID 21192562、化合物

生成物 1

HCID 490481HCID 490481、化合物

実験手順

Butyl 1-(dimethylamino)-6-iodo-4-oxo-1,4-dihydro-3-quinolinecarboxylate (0.50 g) from Preparation No. 58 and 4-chlorobenzylamine (0.29 mL) are heated to 170° C. for 7 hours. The reaction is cooled to rt, and the crude solid is recrystallized in acetic acid yielding 0.54 g of the amide. The resulting amide (0.25 g), copper (I) iodide (30 mg), and bis(triphenylphosphine)palladium (II) chloride (18 mg) are suspended in diethylamine (8 mL). Propargyl alcohol (36 μL) is added and the mixture is allowed to stir at room temperature for 16 h. The mixture is diluted with ethanol and then concentrated in vacuo. The crude solid is triturated with dichloromethane and purified by column chromatography (2% MeOH/CH2Cl2), affording 9 mg of the title compound as a beige solid.

後処理

  1. customthe crude solid is recrystallized in acetic acid yielding 0.54 g of the amide
  2. additionPropargyl alcohol (36 μL) is added
  3. additionThe mixture is diluted with ethanol
  4. concentrationconcentrated in vacuo
  5. customThe crude solid is triturated with dichloromethane
  6. custompurified by column chromatography (2% MeOH/CH2Cl2)

出典と根拠

ORDレコード
ord-f8df5206534348c096e9cb4c04bdafcc
出典データセット
uspto-grants-2001_06
特許番号
US06248739B1

反応ノート

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