Dimethyl Sulfate → 1-(4,5-Dimethoxy-2-methoxycarbonylphenyl)-3,4-dihydroisoquinoline

HRID 65689ノート

反応式

HRID 65689 の反応式
S([O:6][CH3:7])(OC)(=O)=O.O[C:9]12[C:25]3[C:20](=[CH:21][C:22]([O:28][CH3:29])=[C:23]([O:26][CH3:27])[CH:24]=3)[C:19](=[O:30])[N:10]1[CH2:11][CH2:12][C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][C:18]=12>CO>[CH3:29][O:28][C:22]1[C:23]([O:26][CH3:27])=[CH:24][C:25]([C:9]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH2:12][CH2:11][N:10]=2)=[C:20]([C:19]([O:6][CH3:7])=[O:30])[CH:21]=1

参加物

4

反応物 2

HCID 6497Dimethyl SulfateHCID 2275755212b-Hydroxy-10,11-dimethoxy-5,6,8,12b-tetrahydro-isoindolo[1,2-a]isoquinol-8-one

生成物 1

HCID 227575571-(4,5-Dimethoxy-2-methoxycarbonylphenyl)-3,4-dihydroisoquinoline

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

Dimethyl sulphate (48 cc) is added to a suspension of 12b-hydroxy-10,11-dimethoxy-5,6,8,12b-tetrahydroisoindolo[1,2-a]isoquinol-8-one (80.65 g) in methanol (563 cc) and the reaction mixture is heated under reflux for 6 hours. After concentration to 100 cc and the successive addition of water (300 cc) and then of 10N sodium hydroxide (70 cc), the mixture is extracted three times with ethyl acetate (total 400 cc). The combined organic solutions are washed three times with distilled water (total 400 cc), dried over anhydrous sodium sulphate, treated with decolourising charcoal (1 g), filtered and evaporated. 1-(4,5-Dimethoxy-2-methoxycarbonylphenyl)-3,4-dihydroisoquinoline (67.8 g), melting at 133° C., is thus obtained.

後処理

  1. temperaturethe reaction mixture is heated
  2. temperatureunder reflux for 6 hours
  3. concentrationAfter concentration to 100 cc
  4. additionthe successive addition of water (300 cc)
  5. extractionof 10N sodium hydroxide (70 cc), the mixture is extracted three times with ethyl acetate (total 400 cc)
  6. washThe combined organic solutions are washed three times with distilled water (total 400 cc)
  7. dry with materialdried over anhydrous sodium sulphate
  8. additiontreated with decolourising charcoal (1 g)
  9. filtrationfiltered
  10. customevaporated

出典と根拠

ORDレコード
ord-6f9b99b6e68b4a00819632ca9a5ba3aa
出典データセット
uspto-grants-1978_12
特許番号
US04128650

反応ノート

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