Phosphorus oxychloride → Methyl 1-chloroisoquinoline-5-carboxylate

HRID 1051273ノート

反応式

HRID 1051273 の反応式
[CH3:1][O:2][C:3]([C:5]1[CH:14]=[CH:13][CH:12]=[C:11]2[C:6]=1[CH:7]=[CH:8][N+:9]([O-])=[CH:10]2)=[O:4].O=P(Cl)(Cl)[Cl:18]>ClCCl>[Cl:18][C:10]1[C:11]2[CH:12]=[CH:13][CH:14]=[C:5]([C:3]([O:2][CH3:1])=[O:4])[C:6]=2[CH:7]=[CH:8][N:9]=1

参加物

4

反応物 2

HCID 24813Phosphorus oxychlorideHCID 1180908815-(Methoxycarbonyl)isoquinoline 2-oxide

生成物 1

HCID 72213626Methyl 1-chloroisoquinoline-5-carboxylate収率 86%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
90 °C

実験手順

5-(Methoxycarbonyl)isoquinoline 2-oxide (2 g, 9.84 mmol) obtained in Step (4) of Preparation Example 1 was dissolved in dichloromethane (20 mL), added with POCl3 (20 mL) at room temperature, and stirred for 4 hours or more at 90° C. The temperature of the reaction mixture was lowered to room temperature, followed by quenching with distilled water. The reaction mixture was diluted with dichloromethane, and washed with a saturated aqueous sodium bicarbonate solution and saline. The organic layer thus obtained was dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure to obtain the title compound (1.86 g, 86%).

後処理

  1. customwas lowered to room temperature
  2. customby quenching with distilled water
  3. additionThe reaction mixture was diluted with dichloromethane
  4. washwashed with a saturated aqueous sodium bicarbonate solution and saline
  5. customThe organic layer thus obtained
  6. dry with materialwas dried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-51f304266d784ea59cc32b001902bdf9
出典データセット
uspto-grants-2016_07
特許番号
US09388165B2

反応ノート

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