Sulfuric Acid → Indole, 3-(2-aminoethyl)-6-chloro-5-methoxy-
Reaction equation
[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]Participants
Procedure
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.
Workup
- waitto proceed for another hour
- additionThe mixture then was poured into ice
- extractionThe resulting mixture was extracted with several portions of chloroform
- washThe extracts were washed with sodium chloride solution
- dry with materialdried over sodium sulfate
- customthe solvent was removed in vacuo
- additiona small amount of pentane was added
- temperatureThe mixture was cooled
- filtrationthe crystalline product collected by filtration
- customAfter drying
Sources & evidence
- ORD record
- ord-66517901ea824d6585a2aa86ce23b8eb
- Source dataset
- uspto-grants-1978_05
- Patent number
- US04087444
Reaction notes
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