Sulfuric Acid → Indole, 3-(2-aminoethyl)-6-chloro-5-methoxy-

HRID 371680노트

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HRID 371680 반응식
[H-].[Al+3].[Li+].[H-].[H-].[H-].S(=O)(=O)(O)O.[C:12]([CH2:14][C:15]1[C:23]2[C:18](=[CH:19][C:20]([Cl:26])=[C:21]([O:24][CH3:25])[CH:22]=2)[NH:17][CH:16]=1)#[N:13].[OH-].[Na+]>O1CCCC1>[CH3:25][O:24][C:21]1[CH:22]=[C:23]2[C:18]([NH:17][CH:16]=[C:15]2[CH2:14][CH2:12][NH2:13])=[CH:19][C:20]=1[Cl:26]

참가 물질

6

반응물 4

HCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 203555806-Chloro-5-methoxy-1H-indole-3-acetonitrileHCID 21226445Aluminium lithium hydride

생성물 1

HCID 18947310Indole, 3-(2-aminoethyl)-6-chloro-5-methoxy-수율 83%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매3회

실험 절차

A solution 7.6 g. (0.2 mole) of lithium aluminum hydride in 200 ml. of tetrahydrofuran was stirred under nitrogen while a solution of 5.2 ml. (9.8 g., 0.1 mole) of 100 percent sulfuric acid in 40 ml. of tetrahydrofuran was added. A solution of 6.0 g. (27 mmoles) of 3-cyanomethyl-5-methoxy-6-chloroindole in 40 ml. of tetrahydrofuran then was added over a 30-minute period. The reaction was allowed to proceed for another hour with stirring. The mixture then was poured into ice followed by 20 percent sodium hydroxide solution. The resulting mixture was extracted with several portions of chloroform. The extracts were washed with sodium chloride solution, dried over sodium sulfate, and the solvent was removed in vacuo. The residue was boiled in ether, and a small amount of pentane was added. The mixture was cooled, and the crystalline product collected by filtration. After drying, 5.04 g. (83 percent) of 5-methoxy-6-chlorotryptamine were obtained.

후처리

  1. waitto proceed for another hour
  2. additionThe mixture then was poured into ice
  3. extractionThe resulting mixture was extracted with several portions of chloroform
  4. washThe extracts were washed with sodium chloride solution
  5. dry with materialdried over sodium sulfate
  6. customthe solvent was removed in vacuo
  7. additiona small amount of pentane was added
  8. temperatureThe mixture was cooled
  9. filtrationthe crystalline product collected by filtration
  10. customAfter drying

출처 및 근거

ORD 기록
ord-66517901ea824d6585a2aa86ce23b8eb
출처 데이터셋
uspto-grants-1978_05
특허 번호
US04087444

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