Phosphorus oxychloride → 7-Bromo-1-Chloroisoquinoline

HRID 551273ノート

反応式

HRID 551273 の反応式
[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][NH:8][C:9]2=O)=[CH:4][CH:3]=1.P(Cl)(Cl)([Cl:15])=O.C(=O)([O-])O.[Na+]>C(Cl)(Cl)Cl>[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][N:8]=[C:9]2[Cl:15])=[CH:4][CH:3]=1

参加物

5

反応物 3

HCID 24813Phosphorus oxychlorideHCID 516892Sodium BicarbonateHCID 112761337-Bromoisoquinolin-1-ol

生成物 1

HCID 65020247-Bromo-1-Chloroisoquinoline収率 61.9%

試薬・触媒・溶媒 1

HCID 6212Chloroform溶媒

反応条件

温度
100 °C

実験手順

7-Bromo-2H-isoquinolin-1-one (3.0 g, 13.4 mmol), phosphorus oxychloride (8.22 g, 53.6 mmol), and chloroform (25 mL) combined in a sealed tube and heated with stirring at 100° C. for 4 hours. Cooled to ˜60° C., poured into ice water (100 mL), neutralized carefully with saturated aqueous sodium hydrogencarbonate, extracted into methylene chloride and dried over magnesium sulfate. Flash column chromatography on silica gel gave the product as a pale cream solid (2.01 g, 8.3 mmol). 1H NMR (CDCl3) δ 8.51 (d, 1H), 8.30 (d, 1H), 7.82 (dd, 1H), 7.72 (d, 1H), 7.57 (dd, 1H). ESI MS (M+1)+: 242, 244, 246 (Br, Cl).

後処理

  1. temperatureheated
  2. temperatureCooled to ˜60° C.
  3. extractionextracted into methylene chloride
  4. dry with materialdried over magnesium sulfate

出典と根拠

ORDレコード
ord-2264de8a5346429cb01dc3bcb5f89043
出典データセット
uspto-grants-2011_05
特許番号
US07947684B2

反応ノート

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