Sulfuric Acid → 6-Methoxy-4-(3,4-dimethoxyphenyl)-1,2,3,4-tetrahydroisoquinoline

HRID 1089469ノート

反応式

HRID 1089469 の反応式
[CH3:1][O:2][C:3]1[CH:23]=[CH:22][C:6]([CH2:7][NH:8][CH2:9][CH:10](O)[C:11]2[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[C:13]([O:19][CH3:20])[CH:12]=2)=[CH:5][CH:4]=1.S(=O)(=O)(O)O>FC(F)(F)C(O)=O>[CH3:1][O:2][C:3]1[CH:23]=[C:22]2[C:6](=[CH:5][CH:4]=1)[CH2:7][NH:8][CH2:9][CH:10]2[C:11]1[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[C:13]([O:19][CH3:20])[CH:12]=1

参加物

4

反応物 2

HCID 1118Sulfuric AcidHCID 14719544HCID 14719544、化合物

生成物 1

HCID 147195466-Methoxy-4-(3,4-dimethoxyphenyl)-1,2,3,4-tetrahydroisoquinoline収率 88.2%

試薬・触媒・溶媒 1

HCID 6422Trifluoroacetic acid溶媒

実験手順

α-[[(4-methoxybenzyl)amino]methyl]-3,4-dimethoxybenzyl alcohol (950 mg) was dissolved in 7.2 ml of trifluoroacetic acid, and after adding thereto 0.22 ml of conc. sulfuric acid under cie cooling, the reaction was allowed to react for 45 minutes. The reaction solution was concentrated, and subjected to azeotropic distillation with toluene 2 times. After adding chloroform, the mixture was basified by addition of 28% aqueous ammonia under ice cooling. By a separating procedure, the chloroform layer was collected, washed with water, and dried over anhydrous sodium sulfate. The solvent was distilled off, and the residue obtained was subjected to silica gel column chromatography (chlroform-methanol-28% aqueous ammonia=15:1:0.1), giving 790 mg of 6-methoxy-4-(3,4-dimethoxyphenyl)-1,2,3,4-tetrahydroisoquinoline as oily matter.

後処理

  1. additionafter adding
  2. customto react for 45 minutes
  3. concentrationThe reaction solution was concentrated
  4. distillationsubjected to azeotropic distillation with toluene 2 times
  5. additionAfter adding chloroform
  6. additionthe mixture was basified by addition of 28% aqueous ammonia under ice cooling
  7. customBy a separating procedure, the chloroform layer was collected
  8. washwashed with water
  9. dry with materialdried over anhydrous sodium sulfate
  10. distillationThe solvent was distilled off
  11. customthe residue obtained

出典と根拠

ORDレコード
ord-1219b06e97364ac195d35d9f6d8ed28e
出典データセット
uspto-grants-1990_10
特許番号
US04966904

反応ノート

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