Sulfuric Acid → 7,8-Dimethoxy-4-(3,4-dimethoxyphenyl)-1,2,3,4-tetrahydroisoquinoline

HRID 1089798노트

반응식

HRID 1089798 반응식
[CH3:1][O:2][C:3]1[C:23]([O:24][CH3:25])=[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>FC(F)(F)C(O)=O>[CH3:25][O:24][C:23]1[C:3]([O:2][CH3:1])=[C:4]2[C:20]([CH:8]([C:9]3[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[C:11]([O:17][CH3:18])[CH:10]=3)[CH2:7][NH:6][CH2:5]2)=[CH:21][CH:22]=1

참가 물질

4

반응물 2

HCID 1118Sulfuric AcidHCID 14719553alpha-[[(2,3-Dimethoxybenzyl)amino]methyl]-3,4-dimethoxybenzyl alcohol

생성물 1

HCID 147195577,8-Dimethoxy-4-(3,4-dimethoxyphenyl)-1,2,3,4-tetrahydroisoquinoline수율 79.1%

시약·촉매·용매 1

HCID 6422Trifluoroacetic acid용매

실험 절차

1.0 g of α-[[(2,3-dimethoxybenzyl)amino]methyl]-3,4-dimethoxybenzyl alcohol was dissolved in 7.5 ml of trifluoroacetic acid, and after adding thereto 0.23 ml of conc. sulfuric acid under ice cooling, the mixture was allowed to react for 30 minutes. The reaction solution was concentrated, and subjected to azeotropic distillation with toluene 2 times. After adding to the mixture chloroform, the mixture was basified by addition of 28% aqueous ammonia under ice cooling. After a separating procedure, the chloroform layer was collected, washed with water, and dried over anhydrous magnesium sulfate. The solvent was distilled off, and the residue thus obtained was recrystallized from chloroform-n-hexane, affording 750 mg of 7,8-dimethoxy-4-(3,4-dimethoxyphenyl)-1,2,3,4-tetrahydroisoquinoline (m.p. 109°-110° C.).

후처리

  1. additionafter adding
  2. customto react for 30 minutes
  3. concentrationThe reaction solution was concentrated
  4. distillationsubjected to azeotropic distillation with toluene 2 times
  5. additionAfter adding to the mixture chloroform
  6. additionthe mixture was basified by addition of 28% aqueous ammonia under ice cooling
  7. customAfter a separating procedure, the chloroform layer was collected
  8. washwashed with water
  9. dry with materialdried over anhydrous magnesium sulfate
  10. distillationThe solvent was distilled off
  11. customthe residue thus obtained
  12. customwas recrystallized from chloroform-n-hexane

출처 및 근거

ORD 기록
ord-7908571185614160a71dbffd5787d798
출처 데이터셋
uspto-grants-1992_01
특허 번호
US05079256

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