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

HRID 1461836노트

반응식

HRID 1461836 반응식
[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.C(Cl)(Cl)Cl.CO>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

참가 물질

5

반응물 3

HCID 1118Sulfuric AcidHCID 14719544HCID 14719544, 화합물HCID 21584188Chloroform methanol

생성물 1

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

시약·촉매·용매 1

HCID 6422Trifluoroacetic acid용매

실험 절차

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 ice 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 (chloroform-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.

후처리

  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

출처 및 근거

ORD 기록
ord-78c24c6e540e49fa8e3c578015673c9a
출처 데이터셋
uspto-grants-1991_12
특허 번호
US05077406

반응 노트

불러오는 중…