Benzoyl chloride → 2-Benzoyl-6,7-dichloro-1-cyano-1,2-dihydroisoquinoline

HRID 247398

反応式

HRID 247398 の反応式
Cl.[Cl:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[Cl:13])[CH:9]=[N:8][CH:7]=[CH:6]2.C1OCCOCCOCCOCCOCCOC1.[C-:32]#[N:33].[K+].[C:35](Cl)(=[O:42])[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1>C(Cl)Cl.O>[C:35]([N:8]1[CH:7]=[CH:6][C:5]2[C:10](=[CH:11][C:12]([Cl:13])=[C:3]([Cl:2])[CH:4]=2)[CH:9]1[C:32]#[N:33])(=[O:42])[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1

参加物

7

反応物 4

HCID 7412Benzoyl chlorideHCID 9032Potassium CyanideHCID 2855718-Crown-6HCID 125950596,7-Dichloroisoquinoline hydrochloride

生成物 1

HCID 136795062-Benzoyl-6,7-dichloro-1-cyano-1,2-dihydroisoquinoline

試薬・触媒・溶媒 2

HCID 962Water溶媒2 回HCID 6344Dichloromethane溶媒3 回

実験手順

To a stirred suspension of 1.7 g (8.6 mmole) of 6,7-dichloroisoquinoline hydrochloride in 12 ml of methylene chloride was added 0.11 g (0.43 mmole) of 18-crown-6 followed by a solution of 1.67 g (26 mmole) of potassium cyanide in 12 ml of water. The mixture was stirred vigorously under nitrogen for 30 minutes and then a solution of 2.4 g (17.2 mmole) of benzoyl chloride in 10 ml of methylene chloride was added dropwise. After the reaction mixture was stirred at ambient temperature, under nitrogen for 3 hours, an additional 50 ml of methylene chloride and 50 ml of water was added. The organic phase was separated, washed successively with water, 5% aqueous sodium bicarbonate solution, water and brine. The solution was dried over magnesium sulfate and concentrated. The resulting oil was triturated with methanol at 0° C. to give 2-benzoyl-6,7-dichloro-1-cyano-1,2-dihydroisoquinoline, m.p. 194°-196° C.

後処理

  1. stirringAfter the reaction mixture was stirred at ambient temperature, under nitrogen for 3 hours
  2. customThe organic phase was separated
  3. washwashed successively with water, 5% aqueous sodium bicarbonate solution, water and brine
  4. dry with materialThe solution was dried over magnesium sulfate
  5. concentrationconcentrated
  6. customThe resulting oil was triturated with methanol at 0° C.

出典と根拠

ORDレコード
ord-4e2f39a4ec464fbd86bcee1c25d0dc78
出典データセット
uspto-grants-1987_11
特許番号
US04707485

関連ノート

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