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

HRID 51970

反応式

HRID 51970 の反応式
[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]

参加物

8

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 1140Toluene溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
100 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-144721e4be144da69663e9a5f1c7b55f
出典データセット
uspto-grants-2004_03
特許番号
US06713489B2

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