Sulfuric Acid → N-(2-methoxy-3,4-methylenedioxybenzyl)-N-(p-toluenesulfonyl)aminoacetaldehyde diethylacetal

HRID 622194노트

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HRID 622194 반응식
[CH2:1]([O:3][CH:4]([O:19][CH2:20][CH3:21])[CH2:5][NH:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]2[O:14][CH2:15][O:16][C:10]=2[C:9]=1[O:17][CH3:18])[CH3:2].[OH-].[Na+].[S:24](=[O:28])(=O)(O)[OH:25]>>[CH2:20]([O:19][CH:4]([O:3][CH2:1][CH3:2])[CH2:5][N:6]([CH2:7][C:8]1[CH:13]=[CH:12][C:11]2[O:14][CH2:15][O:16][C:10]=2[C:9]=1[O:17][CH3:18])[S:24]([C:11]1[CH:12]=[CH:13][C:8]([CH3:7])=[CH:9][CH:10]=1)(=[O:28])=[O:25])[CH3:21]

참가 물질

4

반응물 3

HCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 13911324HCID 13911324, 화합물

생성물 1

HCID 13911325N-(2-methoxy-3,4-methylenedioxybenzyl)-N-(p-toluenesulfonyl)aminoacetaldehyde diethylacetal수율 83%

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온도
5 °C

실험 절차

62.29 g (0.2 mol) of N-(2-methoxy-3,4-methylenedioxybenzyl)-N-methylaminoacetaldehyde dimethylacetal (1) obtained in Example 2 was dissolved in 400 ml of 6N sulfuric acid. After stirring at 76°-78° C. for 1.5 hours, the reaction mixture was cooled and pH was adjusted to about 11 by adding 25% aqueous solution of sodium hydroxide at temperature lower than 30° C. It was extracted with 200 ml and then 100 ml of methylene chloride successively, which were combined and washed with 100 ml of water and then dried over anhydrous magnesium sulfate. The salt was filtered out and the filtrate was concentrated under vacuum. The residue was dissolved under heating by adding 120 ml of ethanol and then cooled to 5° C. to deposit crystals. The crystals were collected by filtration, washed with 30 ml of cold ethanol and then dried under vacuum to obtain 38.09 g (yield 83%) of 4-hydroxy-8-methoxy-2-methyl- 6,7-methylenedioxy-1,2,3,4-tetrahydroisoquinoline (2), m.p. 152°-3° C. IR and NMR spectra of the resultant product are listed below. ##STR35##

후처리

  1. temperaturethe reaction mixture was cooled
  2. extractionIt was extracted with 200 ml
  3. washwashed with 100 ml of water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationThe salt was filtered out
  6. concentrationthe filtrate was concentrated under vacuum
  7. dissolutionThe residue was dissolved
  8. temperatureunder heating
  9. additionby adding 120 ml of ethanol
  10. filtrationThe crystals were collected by filtration
  11. washwashed with 30 ml of cold ethanol
  12. customdried under vacuum

출처 및 근거

ORD 기록
ord-97b4a90d120947cd8df707a55970f62a
출처 데이터셋
uspto-grants-1988_09
특허 번호
US04769480

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