Sulfuric Acid → 4-(6-Fluoro-3,4-dimethoxyphenyl)-7,8-dimethoxy-1,2,3,4-tetrahydroisoquinoline

HRID 54677노트

반응식

HRID 54677 반응식
[CH3:1][O:2][C:3]1[C:24]([O:25][CH3:26])=[CH:23][CH:22]=[CH:21][C:4]=1[CH2:5][NH:6][CH2:7][CH:8](O)[C:9]1[C:14]([F:15])=[CH:13][C:12]([O:16][CH3:17])=[C:11]([O:18][CH3:19])[CH:10]=1.S(=O)(=O)(O)O.C([O-])(=O)C.[Na+]>FC(F)(F)C(O)=O>[F:15][C:14]1[C:9]([CH:8]2[C:21]3[C:4](=[C:3]([O:2][CH3:1])[C:24]([O:25][CH3:26])=[CH:23][CH:22]=3)[CH2:5][NH:6][CH2:7]2)=[CH:10][C:11]([O:18][CH3:19])=[C:12]([O:16][CH3:17])[CH:13]=1

참가 물질

5

반응물 3

HCID 1118Sulfuric AcidHCID 517045Sodium AcetateHCID 14719568alpha-[[(2,3-Dimethoxybenzyl)amino]methyl]-6-fluoro-3,4-dimethoxybenzyl alcohol

생성물 1

HCID 199597004-(6-Fluoro-3,4-dimethoxyphenyl)-7,8-dimethoxy-1,2,3,4-tetrahydroisoquinoline수율 98.9%

시약·촉매·용매 1

HCID 6422Trifluoroacetic acid용매

실험 절차

α-[[(2,3-dimethoxybenzyl)amino]methyl]-6-fluoro-3,4-dimethoxybenzyl alcohol (1.0 g) was dissolved in 7 ml of trifluoroacetic acid, and after adding thereto under ice cooling, conc. sulfuric acid (0.25 ml), the mixture was stirred for 40 minutes. 0.72 g of sodium acetate was added to the reaction mixture, and the mixture was concentrated. To the residue was added chloroform and water, and the mixture was basified by addition of conc. aqueous ammonia under ice cooling. After separating procedure, the chloroform layer was collected, washed with saturated aqueous NaCl solution, and dried over anhydrous sodium sulfate. The solvent was distilled off, 0.94 g of 4-(6-fluoro-3,4-dimethoxyphenyl)-7,8-dimethoxy-1,2,3,4-tetrahydroisoquinoline was obtained as a syrupy matter.

후처리

  1. additionafter adding
  2. concentrationthe mixture was concentrated
  3. additionTo the residue was added chloroform and water
  4. additionthe mixture was basified by addition of conc. aqueous ammonia under ice cooling
  5. customAfter separating procedure
  6. customthe chloroform layer was collected
  7. washwashed with saturated aqueous NaCl solution
  8. dry with materialdried over anhydrous sodium sulfate
  9. distillationThe solvent was distilled off

출처 및 근거

ORD 기록
ord-06f55568dca04ddcaa9d07adbba43c91
출처 데이터셋
uspto-grants-1997_04
특허 번호
US05623074

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