7,8-Dichloro-1,2,3,4-tetrahydroisoquinoline hydrochloride → 7,8-Dichloro-3,4-dihydroisoquinoline

HRID 2058428ノート

反応式

HRID 2058428 の反応式
N(S([O-])(=O)=O)(S([O-])(=O)=O)[O].[K+].[K+].Cl.[Cl:14][C:15]1[C:24]([Cl:25])=[C:23]2[C:18]([CH2:19][CH2:20][NH:21][CH2:22]2)=[CH:17][CH:16]=1>C(=O)([O-])[O-].[Na+].[Na+]>[Cl:14][C:15]1[C:24]([Cl:25])=[C:23]2[C:18]([CH2:19][CH2:20][N:21]=[CH:22]2)=[CH:17][CH:16]=1

参加物

4

反応物 2

HCID 1239197,8-Dichloro-1,2,3,4-tetrahydroisoquinoline hydrochlorideHCID 3032624Potassium nitrosodisulfonate

生成物 1

HCID 128184197,8-Dichloro-3,4-dihydroisoquinoline

試薬・触媒・溶媒 1

HCID 10340Sodium Carbonate溶媒2 回

実験手順

To a mixture of 1 liter 5 percent aqueous sodium carbonate and 62.6 g. (0.233 mole) potassium nitrosodisulfonate was added 21.9 g. (0.092 mole) 7,8-dichloro-1,2,3,4-tetrahydroisoquinoline hydrochloride and then 0.1 liter 5 percent aqueous sodium carbonate. The reaction mixture was stirred at room temperature for 23 hours. The reaction mixture was then extracted with methylene chloride (3×250 ml.). The combined extract was washed with saturated sodium chloride solution, dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated to dryness under reduced pressure to afford a crude intermediate. The crude intermediate was recrystallized from ethyl acetate to yield 7,8-dichloro-3,4-dihydroisoquinoline as a yellow solid with a melting point of 56°-60° C. 7,8-Dichloro-3,4-dihydro isoquinoline was converted to the desired 7,8-dichloro-1-isopropyl-1,2,3,4-tetrahydroisoquinoline via a Grignard reaction with isopropylmagnesium iodide. 7,8-Dichloro-1-isopropyl-1,2,3,4-tetrahydroisoquinoline hydrochloride has a melting point of 196°-200° C.

後処理

  1. extractionThe reaction mixture was then extracted with methylene chloride (3×250 ml.)
  2. extractionThe combined extract
  3. washwas washed with saturated sodium chloride solution
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated to dryness under reduced pressure
  7. customto afford a crude intermediate
  8. customThe crude intermediate was recrystallized from ethyl acetate

出典と根拠

ORDレコード
ord-834bd13d095941d1afc95ab219d50cde
出典データセット
uspto-grants-1982_03
特許番号
US04317826

反応ノート

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