Triethylamine → 6-Fluoro-7-methylisoquinolin-1(2H)-one

HRID 2402590ノート

反応式

HRID 2402590 の反応式
[F:1][C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][C:12]=1[CH3:13])[CH:5]=[CH:6]C(O)=O.C([N:16]([CH2:19]C)CC)C.ClC(OCC)=[O:23].[N-]=[N+]=[N-].[Na+]>CC(C)=O.O.C(Cl)(Cl)Cl>[F:1][C:2]1[CH:3]=[C:4]2[C:10](=[CH:11][C:12]=1[CH3:13])[C:19](=[O:23])[NH:16][CH:6]=[CH:5]2

参加物

8

反応物 4

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 33557Sodium AzideHCID 27746083-Fluoro-4-methylcinnamic acid

生成物 1

HCID 592260506-Fluoro-7-methylisoquinolin-1(2H)-one収率 41.7%

試薬・触媒・溶媒 3

HCID 180Acetone溶媒2 回HCID 962Water溶媒HCID 6212Chloroform溶媒

反応条件

温度
150 °C

実験手順

To a solution of 10.0 g (55.5 mmol) of 3-fluoro-4-methyl-cinnamic acid in 80 ml of acetone were subsequently added at 0° C. 6.74 g (66.6 mmol) of triethylamine in 10 ml of acetone followed by 7.83 g (72.2 mmol) of ethyl chloroformate. After stirring for 2 h at 0 to 5° C. a solution of 4.0 g (61.1 mmol) of sodium azide in 9.5 ml of water was added. After stirring for 1 additional h the reaction mixture was poured onto 200 ml of ice water and extraced twice with chloroform. The organic phase was dried over magnesium sulfate, 40 ml diphenylether were added and the chloroform was cautiously removed in vacuo. The residue was then added dropwise into 50 ml of diphenylether, which had been preheated to 245° C. After complete addition it was stirred further for 1 h at 230-250° C. After cooling down to 150° C. the reaction mixture was poured into 270 ml of heptane and after further cooling in an ice bath the precipitated product was filtered by suction and 4.1 g 6-fluoro-7-methyl-2H-isoquinolin-1-one were obtained.

後処理

  1. additionwas added
  2. dry with materialThe organic phase was dried over magnesium sulfate, 40 ml diphenylether
  3. additionwere added
  4. customthe chloroform was cautiously removed in vacuo
  5. additionThe residue was then added dropwise into 50 ml of diphenylether, which
  6. customhad been preheated to 245° C
  7. additionAfter complete addition it
  8. stirringwas stirred further for 1 h at 230-250° C
  9. additionwas poured into 270 ml of heptane
  10. temperatureafter further cooling in an ice bath the precipitated product
  11. filtrationwas filtered by suction

出典と根拠

ORDレコード
ord-d49b06d601864e3d89ce94fb0ee9fa6c
出典データセット
uspto-grants-2014_08
特許番号
US08796458B2

反応ノート

読み込み中…