Aluminum(III) Chloride → 3-[(2-Aminoethyl)thio]-7-methylindole

HRID 4313Notes

Reaction equation

HRID 4313 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:10]=1[NH:9][CH:8]=[C:7]2[S:11][CH2:12][C:13]#[N:14].[H-].[Al+3].[Li+].[H-].[H-].[H-].[Al+3].[Cl-].[Cl-].[Cl-]>CCOCC>[NH2:14][CH2:13][CH2:12][S:11][C:7]1[C:6]2[C:10](=[C:2]([CH3:1])[CH:3]=[CH:4][CH:5]=2)[NH:9][CH:8]=1

Participants

5

Reactant 3

HCID 6451240Aluminum(III) ChlorideHCID 201523507-Methylindol-3-ylthioacetonitrileHCID 21226445Aluminium lithium hydride

Product 1

HCID 201523573-[(2-Aminoethyl)thio]-7-methylindole

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

The ether solution was separated and dried over MgSO4. The filtered solution was evaporated in vacuo to give 24.4 g (66%) of 7-methylindol-3-ylthioacetonitrile as a tan solid. An ether solution of 14.1 g (70 mmole) of the nitrile was treated with 2.7 g (70 mmole) of lithium aluminum hydride and 9.5 g (70 mmole) of AlCl3. The dried ether solution was evaporated in vacuo to give 3-[(2-aminoethyl)thio]-7-methylindole which was crystalized from isopropanol to give 6.2 g of tan crystals.

Workup

  1. customThe dried ether solution was evaporated in vacuo

Sources & evidence

ORD record
ord-e1d5c8532bfa4e83949fd6e9d0c8900e
Source dataset
uspto-grants-1988_02
Patent number
US04725604

Reaction notes

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