HCID 86696916、化合物 → 7-(3-Chloropropoxy)-6-methoxyquinolin-4-OL

HRID 1049061ノート

反応式

HRID 1049061 の反応式
[Cl:1][CH2:2][CH2:3][CH2:4][O:5][C:6]1[C:11]([O:12][CH3:13])=[CH:10][C:9]([C:14](=[O:20])/[CH:15]=[CH:16]/N(C)C)=[C:8]([N+:21]([O-])=O)[CH:7]=1>C(O)(=O)C.[Fe]>[Cl:1][CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:7]=[C:8]2[C:9]([C:14](=[O:20])[CH:15]=[CH:16][NH:21]2)=[CH:10][C:11]=1[O:12][CH3:13]

参加物

4

反応物 1

HCID 86696916HCID 86696916、化合物3 回

生成物 1

HCID 717440127-(3-Chloropropoxy)-6-methoxyquinolin-4-OL収率 67.4%

試薬・触媒・溶媒 2

HCID 23925Iron触媒HCID 176Acetic Acid溶媒2 回

反応条件

温度
40 °C

実験手順

0.44 moL of (E)-1-(4-(3-Chloropropoxy)-5-methoxy-2-nitrophenyl)-3-(dimethylamino)prop-2-en-1-one (intermediate IV) (150 g) was dissolved in 1200 mL of glacial acetic acid (8 v/w), and the mixture was heated to 40° C. After intermediate IV was completely dissolve, 2.20 mol (123.1 g) Iron powder was added slowly, then the reaction mixture was heated to 80° C. with mechanical stirring for 2 h. After completion of the reaction, the reaction mixture was filtered immediately to remove iron powder. The filtrate was collected and cooled to precipitate solid, and then filtered to give yellow solid, which was dissolved in glacial acetic acid and the solution was stirred at 80° C. for 30 min then filtered immediately again. The filtrate was cooled to precipitate solid, filtered, and the filter cake was washed with water until the aqueous layer became neutral, dried to give solid 79 g. Yield: 65%.

後処理

  1. temperaturethe reaction mixture was heated to 80° C.
  2. customAfter completion of the reaction
  3. filtrationthe reaction mixture was filtered immediately
  4. customto remove iron powder
  5. customThe filtrate was collected
  6. temperaturecooled
  7. customto precipitate solid
  8. filtrationfiltered
  9. customto give yellow solid, which
  10. stirringthe solution was stirred at 80° C. for 30 min
  11. filtrationthen filtered immediately again
  12. temperatureThe filtrate was cooled
  13. customto precipitate solid
  14. filtrationfiltered
  15. washthe filter cake was washed with water until the aqueous layer
  16. customdried

出典と根拠

ORDレコード
ord-bb1a1ddfea874552b0d771e987bf5618
出典データセット
uspto-grants-2016_07
特許番号
US09382232B2

反応ノート

読み込み中…