Hydrochloric Acid → 6-Fluoro-2-methyl-2,3-dihydroquinolin-4(1H)-one

HRID 2072392ノート

反応式

HRID 2072392 の反応式
[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][CH:6]=[C:5]2[O:12]C.[CH3:14][Li].Cl>O1CCCC1.C(OCC)C>[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH:7]([CH3:14])[CH2:6][C:5]2=[O:12]

参加物

6

反応物 3

HCID 313Hydrochloric AcidHCID 214081816-Fluoro-4-methoxyquinolineHCID 178418348HCID 178418348、化合物2 回

生成物 1

HCID 214081896-Fluoro-2-methyl-2,3-dihydroquinolin-4(1H)-one収率 37%

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-20 °C

実験手順

A stirred solution of 25.8 g (0.146 mole) of 6-fluoro-4-methoxyquinoline from example 3 in 300 ml of tetrahydrofuran was heated under a nitrogen atmosphere to its reflux temperature and then cooled to -20° C. To the cold solution was added 90 ml of 1.82 M methyl lithium in diethyl ether over a period of 0.5 hour. After adding 40 ml of the solution, the reaction temperature was allowed to rise to 0° C. After the addition of methyl lithium was completed, the reaction temperature was allowed to rise to 15° C. The solution was then poured into 1200 ml of a mixture of ice water and hydrochloric acid. After stirring for 0.5 hour the mixture was extracted with about 1200 ml of diethyl ether. The organic layer was dried, filtered and evaporated in vacuo to provide a yellow solid. The product was recrystallized from carbon tetrachloride to give 9.5 g (37% yield) of 6-fluoro-2-methyl-4-oxo-1,2,3,4-tetrahydroquinoline.

後処理

  1. temperaturereflux temperature
  2. customto rise to 0° C
  3. customto rise to 15° C
  4. extractionwas extracted with about 1200 ml of diethyl ether
  5. customThe organic layer was dried
  6. filtrationfiltered
  7. customevaporated in vacuo
  8. customto provide a yellow solid
  9. customThe product was recrystallized from carbon tetrachloride

出典と根拠

ORDレコード
ord-7737a16a86994e9eac007e9dc44092bc
出典データセット
uspto-grants-1977_09
特許番号
US04051247

反応ノート

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