Iodine → 2-iodo-5-propoxy-4H-benzo[f]quinolin-1-one

HRID 68131ノート

反応式

HRID 68131 の反応式
[CH2:1]([O:4][C:5]1[C:14]2[NH:13][CH:12]=[CH:11][C:10](=[O:15])[C:9]=2[C:8]2[CH:16]=[CH:17][CH:18]=[CH:19][C:7]=2[CH:6]=1)[CH2:2][CH3:3].C(=O)([O-])[O-].[K+].[K+].[I:26]I.S([O-])([O-])(=O)=S.[Na+].[Na+]>CN(C=O)C.C(OCC)(=O)C>[I:26][C:11]1[C:10](=[O:15])[C:9]2[C:8]3[CH:16]=[CH:17][CH:18]=[CH:19][C:7]=3[CH:6]=[C:5]([O:4][CH2:1][CH2:2][CH3:3])[C:14]=2[NH:13][CH:12]=1

参加物

7

反応物 4

HCID 807IodineHCID 11430Potassium CarbonateHCID 24477Sodium ThiosulfateHCID 584923735-propoxy-4H-benzo[f]quinolin-1-one

生成物 1

HCID 584923712-iodo-5-propoxy-4H-benzo[f]quinolin-1-one収率 87.4%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

5-Propoxy-4H-benzo[f]quinolin-1-one (2.66 g, 10.5 mmol) was suspended in DMF (20 ml). Potassium carbonate (1.63 g, 11.8 mmol) and iodine (2.95 g, 11.6 mmol) were added to the suspension, followed by stirring at room temperature for 3 hours. The reaction mixture was poured into an aqueous sodium thiosulfate solution (9.14 g, 100 ml), followed by stirring for 5 minutes. Ethyl acetate was added to the reaction mixture and stirred. Subsequently, insoluble matter was collected by filtration, and the filtrate was then separated. The thus-obtained organic layer was washed with an aqueous saturated sodium chloride solution, and then concentrated to dryness under reduced pressure. The residue was added to the collected insoluble matter, followed by purification using silica gel column chromatography (dichloromethane:methanol=50:1→20:1). The purified product was concentrated to dryness under reduced pressure, giving a pale brown powder of 2-iodo-5-propoxy-4H-benzo[f]quinolin-1-one (3.48 g, yield: 87%).

後処理

  1. stirringby stirring for 5 minutes
  2. stirringstirred
  3. filtrationSubsequently, insoluble matter was collected by filtration
  4. customthe filtrate was then separated
  5. washThe thus-obtained organic layer was washed with an aqueous saturated sodium chloride solution
  6. concentrationconcentrated to dryness under reduced pressure
  7. additionThe residue was added to the collected insoluble matter
  8. customfollowed by purification
  9. concentrationThe purified product was concentrated to dryness under reduced pressure

出典と根拠

ORDレコード
ord-12ea6b39e68b49689854239de0fe7cd9
出典データセット
uspto-grants-2014_09
特許番号
USRE045108E1

反応ノート

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