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2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → (9S)-2,3-Dimethyl-9-phenyl-7,8,9,10-tetrahydroimidazo[1,2-h][1,7]naphthyridin-7-one

HRID 584849
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HRID 584849 반응식
[CH3:1][C:2]1[N:3]=[C:4]2[C:13]3[NH:12][C@H:11]([C:14]4[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=4)[CH2:10][C:9](=[O:20])[C:8]=3[CH2:7][CH2:6][N:5]2[C:21]=1[CH3:22].O1CCCC1.ClC1C(=O)C(C#N)=C(C#N)C(=O)C=1Cl.[OH-].[Na+]>C1(C)C=CC=CC=1.C(OCC)(=O)C>[CH3:1][C:2]1[N:3]=[C:4]2[C:13]3[NH:12][C@H:11]([C:14]4[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=4)[CH2:10][C:9](=[O:20])[C:8]=3[CH:7]=[CH:6][N:5]2[C:21]=1[CH3:22]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 69288840(9S)-2,3-Dimethyl-9-phenyl-5,6,7,8,9,10-hexahydroimidazo[1,2-h][1,7]naphthyridin-7-one

생성물 1

HCID 69291849(9S)-2,3-Dimethyl-9-phenyl-7,8,9,10-tetrahydroimidazo[1,2-h][1,7]naphthyridin-7-one수율 32%

시약·촉매·용매 2

HCID 1140Toluene용매HCID 8857Ethyl Acetate용매

실험 절차

63.5 g (0.22 mol) of (9S)-2,3-dimethyl-9-phenyl-5,6,7,8,9,10-hexahydroimidazo[1,2-h][1,7]naphthyridin-7-one are dissolved in 250 ml of toluene and 250 ml of tetrahydrofuran and cooled to 0° C. 59 g (0.26 mol) of 2,3-dichloro-5,6-dicyano-1,4-benzoquinone are introduced in portions of 10 g over a period of 1 h with mechanical stirring. The reaction mixture is stirred at room temperature for 16 h. 1.2 l of 0.5 N sodium hydroxide solution and 1 l of ethyl acetate are then added dropwise. The organic phase is separated off and washed with water. The aqueous phase is reextracted with ethyl acetate and the combined organic phases are dried over sodium sulfate and evaporated. The residue is crystallized in 300 ml of methanol at 0° C. The solid is filtered off with suction, washed with cold methanol and dried. 20 g (32%) of the title compound are isolated as a slightly yellow solid (m.p. 103-105° C.).

후처리

  1. customThe organic phase is separated off
  2. washwashed with water
  3. dry with materialthe combined organic phases are dried over sodium sulfate
  4. customevaporated
  5. customThe residue is crystallized in 300 ml of methanol at 0° C
  6. filtrationThe solid is filtered off with suction
  7. washwashed with cold methanol
  8. customdried

출처 및 근거

ORD 기록
ord-91432d61316b4b869423a13c1966f2dc
출처 데이터셋
uspto-grants-2005_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06927292B2

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