Benzophenone imine → 7-(Benzhydrylidene-amino)-quinoline-3-carboxylic acid ethyl ester

HRID 431360

반응식

HRID 431360 반응식
[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[N:8][C:9]2[C:14]([CH:15]=1)=[CH:13][CH:12]=[C:11](Cl)[CH:10]=2)=[O:5])[CH3:2].CC(C)([O-])C.[Na+].C1(P(C2CCCCC2)C2C=CC=CC=2C2C=CC=CC=2)CCCCC1.[C:48](=[NH:61])([C:55]1[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=1)[C:49]1[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=1>C(OCC)(=O)C.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1(C)C=CC=CC=1>[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[N:8][C:9]2[C:14]([CH:15]=1)=[CH:13][CH:12]=[C:11]([N:61]=[C:48]([C:49]1[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=1)[C:55]1[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=1)[CH:10]=2)=[O:5])[CH3:2]

참가 물질

8

반응물 4

HCID 136809Benzophenone imineHCID 27342162-(Dicyclohexylphosphino)biphenylHCID 15525916Ethyl 7-chloroquinoline-3-carboxylateHCID 23676156Sodium t-butoxide

생성물 1

HCID 102872307-(Benzhydrylidene-amino)-quinoline-3-carboxylic acid ethyl ester수율 12.3%

시약·촉매·용매 3

HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 1140Toluene용매HCID 8857Ethyl Acetate용매

반응 조건

온도
100 °C

실험 절차

7-Chloro-quinoline-3-carboxylic acid ethyl ester (1 g, 4.24 mmol, 1 equiv), dry sodium t-butoxide (571 mg, 5.94 mmol, 1.4 equiv), tris(dibenzylideneacetone)dipalladium (19.5 mg, 21.2 μmol, 1 mol % equiv), and 2-(dicylcohexylphosphino)biphenyl (30 mg, 84.8 μmol, 4 mol % equiv) were placed in a round bottom flask with a magnetic stir bar. The flask was flushed with nitrogen. Benzophenone imine (783 μL, 4.66 mmol, 1.1 equiv) and toluene (8.5 mL) were added. The flask was fitted with a reflux condenser and the reaction was heated at 100° C. for 12 hours. The reaction mixture was cooled to room temperature and diluted with ethyl acetate (20 mL). The reaction mixture was washed with a saturated sodium bicarbonate solution (25 mL), saturated ammonium chloride solution (25 mL), and brine (25 mL). The organic layer was dried over sodium sulfate and then treated with activated charcoal (Darco G-60®) (1 g). The mixture was filtered through diatomaceous earth and concentrated. The residue was stirred in a minimal amount of isopropanol (about 2 mL) to provide 7-(benzhydrylidene-amino)-quinoline-3-carboxylic acid ethyl ester (199 mg, 12%) as a pale yellow solid.

후처리

  1. customThe flask was flushed with nitrogen
  2. customThe flask was fitted with a reflux condenser
  3. temperatureThe reaction mixture was cooled to room temperature
  4. washThe reaction mixture was washed with a saturated sodium bicarbonate solution (25 mL), saturated ammonium chloride solution (25 mL), and brine (25 mL)
  5. dry with materialThe organic layer was dried over sodium sulfate
  6. additiontreated with activated charcoal (Darco G-60®) (1 g)
  7. filtrationThe mixture was filtered through diatomaceous earth
  8. concentrationconcentrated

출처 및 근거

ORD 기록
ord-8eb4846fce754bd6810d7d17739286eb
출처 데이터셋
uspto-grants-2003_12
특허 번호
US06657065B2

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