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

HRID 271831노트

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HRID 271831 반응식
[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

참가 물질

5

반응물 3

HCID 6228DimethylformamideHCID 598361993-Benzyl-7-chloro-2 iodo-quinolineHCID 178418918HCID 178418918, 화합물

생성물 1

HCID 598361973-Benzyl-7-chloroquinoline-2-carbaldehyde수율 110.5%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
-78 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-bedbda194ea4456c94770f40febc4c85
출처 데이터셋
uspto-grants-2008_11
특허 번호
US07452996B2

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