2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → 6-Fluoro-1,2-dihydroquinolin-2-one

HRID 1191340ノート

反応式

HRID 1191340 の反応式
C(C1C(=O)C(Cl)=C(Cl)C(=O)C=1C#N)#N.[F:15][C:16]1[CH:17]=[C:18]2[C:23](=[CH:24][CH:25]=1)[NH:22][C:21](=[O:26])[CH2:20][CH2:19]2>O1CCOCC1>[F:15][C:16]1[CH:17]=[C:18]2[C:23](=[CH:24][CH:25]=1)[NH:22][C:21](=[O:26])[CH:20]=[CH:19]2

参加物

4

反応物 2

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 136907656-Fluoro-3,4-dihydroquinolin-2(1H)-one

生成物 1

HCID 98340436-Fluoro-1,2-dihydroquinolin-2-one収率 31.2%

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒

実験手順

DDQ (0.38 g, 1.7 mmol) was added to a solution of 6-fluoro-3,4-dihydro-1H-quinolin-2-one (0.18 g, 1.1 mmol) in dioxane (25 mL) and the resulting solution was refluxed for 16 h. The mixture was concentrated, and sat aqueous Na2CO3 (25 mL) was added followed by extraction into an organic mixture (MeOH:CH2Cl2; 1:10, 3×50 mL). The combined organic phase was dried (Na2SO4), filtered, concentrated under reduced pressure and purified by flash CC (SiO2; CH2Cl2/MeOH 20:1) to give the title compound (0.056 g, 31%). 1H NMR (DMSO-D6) δ 11.8 (brs, 1H), 7.85 (d, J=9.4 Hz), 7.50 (dd, J=2.8, 9.2 Hz), 7.43-7.37 (m, 1H), 7.37-7.25 (m, 1H), 6.54 (d, J=9.4 Hz).

後処理

  1. temperaturethe resulting solution was refluxed for 16 h
  2. concentrationThe mixture was concentrated
  3. additionwas added
  4. extractionfollowed by extraction into an organic mixture (MeOH:CH2Cl2; 1:10, 3×50 mL)
  5. dry with materialThe combined organic phase was dried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. custompurified by flash CC (SiO2; CH2Cl2/MeOH 20:1)

出典と根拠

ORDレコード
ord-c4a794c1289d4602a814bba217af5bcc
出典データセット
uspto-grants-2014_03
特許番号
US08680115B2

反応ノート

読み込み中…