2-Benzoyl-1-(3,4,5-trimethoxybenzyl)-6,7-dichloro-1-cyano-1,2-dihydroisoquinoline → 6,7-Dichloro-1-(3,4,5-trimethyoxybenzyl)isoquinoline hydrochloride

HRID 247400

反応式

HRID 247400 の反応式
C([N:9]1[CH:18]=[CH:17][C:16]2[C:11](=[CH:12][C:13]([Cl:20])=[C:14]([Cl:19])[CH:15]=2)[C:10]1([CH2:23][C:24]1[CH:29]=[C:28]([O:30][CH3:31])[C:27]([O:32][CH3:33])=[C:26]([O:34][CH3:35])[CH:25]=1)C#N)(=O)C1C=CC=CC=1>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.C1(C)C=CC=CC=1>[ClH:19].[Cl:19][C:14]1[CH:15]=[C:16]2[C:11](=[CH:12][C:13]=1[Cl:20])[C:10]([CH2:23][C:24]1[CH:25]=[C:26]([O:34][CH3:35])[C:27]([O:32][CH3:33])=[C:28]([O:30][CH3:31])[CH:29]=1)=[N:9][CH:18]=[CH:17]2

参加物

4

反応物 1

HCID 136795072-Benzoyl-1-(3,4,5-trimethoxybenzyl)-6,7-dichloro-1-cyano-1,2-dihydroisoquinoline

生成物 1

HCID 212949006,7-Dichloro-1-(3,4,5-trimethyoxybenzyl)isoquinoline hydrochloride

試薬・触媒・溶媒 2

HCID 66133Benzyl triethylammonium chloride触媒HCID 1140Toluene溶媒

実験手順

Benzyltriethylammonium chloride (0.118 g, 0.517 mmole) was added to a solution of 2.3 g (4.5 mmole) of 2-benzoyl-1-(3,4,5-trimethoxybenzyl)-6,7-dichloro-1-cyano-1, 2-dihydroisoquinoline in 40 ml of toluene. The stirred solution was flushed with nitrogen and then 19 ml of 50% sodium hydroxide solution was added in one portion. The reaction mixture was stirred and refluxed under nitrogen for 1.5 hours; it was then cooled and 25 ml of water and 25 ml of ethyl acetate were added. The organic layer was separated, washed (water, brine), dried (magnesium sulfate) and concentrated. The residue in a small volume of methanol was acidified with hydrogen chloride and ether was added to give 6,7-dichloro-1-(3,4,5-trimethyoxybenzyl)isoquinoline hydrochloride as white crystals, melting at 211°-212° C., after recrystallization from methanol-ether.

後処理

  1. customThe stirred solution was flushed with nitrogen
  2. addition19 ml of 50% sodium hydroxide solution was added in one portion
  3. temperaturerefluxed under nitrogen for 1.5 hours
  4. temperatureit was then cooled
  5. addition25 ml of water and 25 ml of ethyl acetate were added
  6. customThe organic layer was separated
  7. washwashed (water, brine)
  8. dry with materialdried (magnesium sulfate)
  9. concentrationconcentrated
  10. additionwas added

出典と根拠

ORDレコード
ord-8de9cfe62198426d936381af7e3b4d2b
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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