Methanol → 2-Amino-7-hydroxyisoquinolinium 2,4,6-trimethylbenzenesulfonate

HRID 336981

反応式

HRID 336981 の反応式
[I-].[NH2:2][N+:3]1[CH:12]=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=1.[OH:13]C1C=C2C(C=CN=C2)=CC=1.CO.[C:26]1([CH3:39])[CH:31]=[C:30]([CH3:32])[CH:29]=[C:28]([CH3:33])[C:27]=1[S:34]([O:37]N)(=[O:36])=[O:35]>C(Cl)Cl.CCOCC>[CH3:33][C:28]1[CH:29]=[C:30]([CH3:32])[CH:31]=[C:26]([CH3:39])[C:27]=1[S:34]([O-:37])(=[O:36])=[O:35].[NH2:2][N+:3]1[CH:12]=[CH:11][C:10]2[C:5](=[CH:6][C:7]([OH:13])=[CH:8][CH:9]=2)[CH:4]=1

参加物

7

反応物 4

HCID 887MethanolHCID 4597677-IsoquinolinolHCID 108586012-Aminoisoquinolinium IodideHCID 11830845O-(2,4,6-Trimethylbenzenesulfonyl)hydroxylamine

生成物 1

HCID 1176992982-Amino-7-hydroxyisoquinolinium 2,4,6-trimethylbenzenesulfonate収率 60.5%

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒HCID 6344Dichloromethane溶媒2 回

実験手順

O-mesitylene sulfonyl hydroxylamine (MSH) (3) was used to prepare the N-amino salt as an aminating agent as described by Tamura et al., (1972) Tetrahedron Letter. 40: 4133, incorporated herein by reference in its entirety. An ice cooled solution of 7-hydroxyisoquinoline (2.0 g, 13.78 mmol) in 30 mL of dry methylene chloride, and 15 ml of dry methanol was added drop wise to O-mesitylenesulfonylhydroxylamine (2.97 g, 13.78 mmol) in 10 mL of dry methylene chloride over 5 min with stirring. The reaction stirred at 0° C. for 6 h. 70 mL of ether was added and the suspension filtered. The precipitate was recrystallized from ethyl acetate to give 2-amino-7-hydroxyisoquinolinium 2,4,6-trimethylbenzenesulfonate (6) in 60.5% yield.

後処理

  1. stirringThe reaction stirred at 0° C. for 6 h
  2. filtrationthe suspension filtered
  3. customThe precipitate was recrystallized from ethyl acetate

出典と根拠

ORDレコード
ord-dc6594f54f0146059ab7c1b506b027da
出典データセット
uspto-grants-2014_11
特許番号
US08889713B1

関連ノート

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