2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → Ethyl 6-methoxyquinoline-3-carboxylate

HRID 495468노트

반응식

HRID 495468 반응식
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[NH:9][CH2:8][CH:7]([CH2:13]CC(O)=O)[CH2:6]2.C(C1C(=O)C(Cl)=C(Cl)[C:22](=[O:23])[C:21]=1C#N)#N.CC([O:36]C)(C)C>C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]=[CH:8][C:7]([C:13]([O:23][CH2:22][CH3:21])=[O:36])=[CH:6]2

참가 물질

5

반응물 3

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 15413tert-Butyl methyl etherHCID 697413816-Methoxy-3-carboxyethyl-1,2,3,4-tetrahydroquinoline

생성물 1

HCID 304668Ethyl 6-methoxyquinoline-3-carboxylate

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a stirred solution of 6-methoxy-3-carboxyethyl-1,2,3,4-tetrahydroquinoline (Step C, 17.6 g, 0.074 mol) in CH2Cl2 (330 mL) cooled at 5° C., was added DDQ (42.2 g, 0.186 mol) portion-wise. The reaction was stirred at RT for 2 h, then diluted with MTBE (600 mL), washed twice with 1N NaOH and twice with water. Flash chromatography in 20% EtOAc/Hexane yielded 6-methoxy-3-ethoxycarbonylquinoline.

후처리

  1. washwashed twice with 1N NaOH and twice with water

출처 및 근거

ORD 기록
ord-e7176f7d9ed047e3a2f658c6cb7e1de6
출처 데이터셋
uspto-grants-2005_09
특허 번호
US06939874B2

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