Diethyl Malonate → Diethyl (2-chloro-6-methylquinolin-4-yl)propanedioate

HRID 540275노트

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HRID 540275 반응식
[Cl:1][C:2]1[CH:11]=[C:10](Cl)[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([CH3:13])[CH:8]=2)[N:3]=1.[C:14]([O:22][CH2:23][CH3:24])(=[O:21])[CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[Cl:1][C:2]1[CH:11]=[C:10]([CH:15]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[C:14]([O:22][CH2:23][CH3:24])=[O:21])[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([CH3:13])[CH:8]=2)[N:3]=1

참가 물질

5

반응물 3

HCID 7761Diethyl MalonateHCID 11430Potassium CarbonateHCID 27546682,4-Dichloro-6-methylquinoline

생성물 1

HCID 86691430Diethyl (2-chloro-6-methylquinolin-4-yl)propanedioate수율 40%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
70 °C

실험 절차

To a solution of 2,4-dichloro-6-methylquinoline (2.11 g, 10 mmol) and 1,3-diethyl propanedioate (2.64 g, 20 mmol) in N,N-dimethylformamide (40 mL) was added anhydrous potassium carbonate (2.8 g, 20 mmol). The mixture was stirred at 70° C. for 3 hours, then poured into ice/water (100 mL) and extracted with ethyl acetate (100 mL×3). The combined organic layers were washed with brine (150 mL×2), dried over sodium sulfate. The residue was purified by flash column chromatography on silica gel (eluting with 20-30% ethyl acetate in petroleum ether) to afford 1.34 g of the desired product (yield was 40%). MS obsd. (ESI+) [(M+H)+] 336.

후처리

  1. extractionextracted with ethyl acetate (100 mL×3)
  2. washThe combined organic layers were washed with brine (150 mL×2)
  3. dry with materialdried over sodium sulfate
  4. customThe residue was purified by flash column chromatography on silica gel (eluting with 20-30% ethyl acetate in petroleum ether)

출처 및 근거

ORD 기록
ord-e45674f1ab854911bc9eb794cfe44516
출처 데이터셋
uspto-grants-2014_10
특허 번호
US08871756B2

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