Dimethylformamide → 3-Benzyl-7-chloroquinoline-2-carbaldehyde

HRID 271831ノート

反応式

HRID 271831 の反応式
[CH2:1]([C:8]1[C:9](I)=[N:10][C:11]2[C:16]([CH:17]=1)=[CH:15][CH:14]=[C:13]([Cl:18])[CH:12]=2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([Mg]Cl)(C)C.CN([CH:28]=[O:29])C>C1COCC1>[CH2:1]([C:8]1[C:9]([CH:28]=[O:29])=[N:10][C:11]2[C:16]([CH:17]=1)=[CH:15][CH:14]=[C:13]([Cl:18])[CH:12]=2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

5

反応物 3

HCID 6228DimethylformamideHCID 598361993-Benzyl-7-chloro-2 iodo-quinolineHCID 178418918HCID 178418918、化合物

生成物 1

HCID 598361973-Benzyl-7-chloroquinoline-2-carbaldehyde収率 110.5%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-78 °C

実験手順

To a solution of 3-benzyl-7-chloro-2 iodo-quinoline (1.5 g, 3.95 mmol) in 15 mL of anhydrous THF at −78° C., was added isopropylmagnesium chloride (5.93 ml, 11.85 mmol). After stirring at −78° C. for 30 minutes, DMF (1.53 ml, 19.8 mmol) was added. The reaction mixture was allowed to slowly warm to ambient temperature over two hours. It was then quenched with saturated NH4Cl and extracted with ethyl acetate (3×). The combined organic layers were washed with brine, dried over MgSO4, and the solvent was removed in vacuo yielding 1.23 g of 3-benzyl-7-chloroquinoline-2-carbaldehyde 24 as brown oil.

後処理

  1. temperatureto slowly warm to ambient temperature over two hours
  2. customIt was then quenched with saturated NH4Cl
  3. extractionextracted with ethyl acetate (3×)
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over MgSO4
  6. customthe solvent was removed in vacuo

出典と根拠

ORDレコード
ord-bedbda194ea4456c94770f40febc4c85
出典データセット
uspto-grants-2008_11
特許番号
US07452996B2

反応ノート

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