1,2-Dimethylhydrazine → 3-Cyano-1-(4-dimethylamino-benzoyl)-pyrrolo[1,2-a]quinoline

HRID 720430

반응식

HRID 720430 반응식
[C:1]([C:3]1[CH:4]=[C:5]([C:16](=[O:24])[C:17]2[CH:22]=[CH:21][C:20](F)=[CH:19][CH:18]=2)[N:6]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[CH:9]=[CH:8][C:7]=12)#[N:2].CNNC.[CH3:29][N:30](C=O)[CH3:31]>O>[C:1]([C:3]1[CH:4]=[C:5]([C:16](=[O:24])[C:17]2[CH:22]=[CH:21][C:20]([N:30]([CH3:31])[CH3:29])=[CH:19][CH:18]=2)[N:6]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[CH:9]=[CH:8][C:7]=12)#[N:2]

참가 물질

5

반응물 3

HCID 13221,2-DimethylhydrazineHCID 6228DimethylformamideHCID 102676303-Cyano (4-fluoro-benzoyl)-pyrrolo[1,2-a]quinoline

생성물 1

HCID 218921233-Cyano-1-(4-dimethylamino-benzoyl)-pyrrolo[1,2-a]quinoline수율 25%

시약·촉매·용매 1

HCID 962Water용매

실험 절차

A solution of 3-cyano-1-[4-fluoro-benzoyl]-pyrrolo[1,2-a]quinoline (56 mg, 0.18 mmol) and dimethylhydrazine (118 mg, 1.96 mmol) in DMF (5 mL) was refluxed for 24 h. It was diluted with water (50 mL) and extracted with EtOAc (3×20 mL). The combined organic layers were dried, concentrated and the residue was purified by column chromatography (EtOAc/Hexane 6:1) to give 15 mg (25%) of the title compound. 1H NMR (CDCl3): 8.11–8.05–7.95 (m, 3H), 7.82–7.78 (m, 2H), 7.63–7.42 (m, 4H), 7.31 (s, 1H), 6.75 (d, J=9.30 Hz, 2H), 3.14 (s, 6H). MS, 340 (M+1).

후처리

  1. extractionextracted with EtOAc (3×20 mL)
  2. customThe combined organic layers were dried
  3. concentrationconcentrated
  4. customthe residue was purified by column chromatography (EtOAc/Hexane 6:1)

출처 및 근거

ORD 기록
ord-5009080523824638a9d9dbb27028aedd
출처 데이터셋
uspto-grants-2006_11
특허 번호
US07135480B2

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