Sulfuric Acid → 4-(3,4-Dimethoxyphenyl)-8-methyl-1,2,3,4-tetrahydroisoquinoline

HRID 1461842ノート

反応式

HRID 1461842 の反応式
CO[C:3]1[CH:23]=[CH:22][CH:21]=[CH:20][C:4]=1[CH2:5][NH:6][CH2:7][CH:8](O)[C:9]1[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[C:11]([O:17][CH3:18])[CH:10]=1.S(=O)(=O)(O)O.F[C:30](F)(F)C(O)=O>>[CH3:18][O:17][C:11]1[CH:10]=[C:9]([CH:8]2[C:3]3[C:4](=[C:20]([CH3:30])[CH:21]=[CH:22][CH:23]=3)[CH2:5][NH:6][CH2:7]2)[CH:14]=[CH:13][C:12]=1[O:15][CH3:16]

参加物

4

反応物 3

HCID 1118Sulfuric AcidHCID 6422Trifluoroacetic acidHCID 20531701HCID 20531701、化合物

生成物 1

HCID 105170974-(3,4-Dimethoxyphenyl)-8-methyl-1,2,3,4-tetrahydroisoquinoline

実験手順

900 mg of α-[[(2-methoxybenzylamino]methyl]-3,4-dimethoxybenzyl alcohol was dissolved in 7 ml of trifluoroacetic acid, and after adding thereto 0.21 ml of conc. sulfuric acid under ice cooling, the mixture was allowed to react for 60 minutes. The reaction solution was concentrated, and subjected to azeotropic distillation 3 times, and after adding chloroform, the mixture was basified by addition of 28% aqueous ammonia. 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 recrystallized from ethyl acetate-n-hexane, giving 440 mg of 4-(3,4-dimethoxyphenyl)-8-methyl-1,2,3,4-tetrahydroisoquinoline, m.p. 86°-88° C.

後処理

  1. additionafter adding
  2. customto react for 60 minutes
  3. concentrationThe reaction solution was concentrated
  4. distillationsubjected to azeotropic distillation 3 times
  5. additionafter adding chloroform
  6. additionthe mixture was basified by addition of 28% aqueous ammonia
  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
  12. customwas recrystallized from ethyl acetate-n-hexane

出典と根拠

ORDレコード
ord-fa011c218d2645688c338847d86c3685
出典データセット
uspto-grants-1991_12
特許番号
US05077406

反応ノート

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