Ammonia → 2-(1-methyl-1H-indol-3-yl)ethan-1-ol

HRID 127267

Reaction equation

HRID 127267 reaction equation
[NH2-].[Na+].[Na].N.[OH:5][CH2:6][CH2:7][C:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[NH:10][CH:9]=1.[CH3:17]I>C(OCC)C>[CH3:17][N:10]1[C:11]2[C:16](=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:8]([CH2:7][CH2:6][OH:5])=[CH:9]1

Participants

7

Reactant 5

HCID 222Ammonia2×HCID 6328Methyl iodideHCID 10685TryptopholHCID 24533Sodium amideHCID 5360545Sodium

Product 1

HCID 122478062-(1-methyl-1H-indol-3-yl)ethan-1-ol

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a solution of sodium amide from 0.63 g sodium in 50 ml liquid ammonia is added in dropwise fashion a solution of 3.22 g of 3-(2-hydroxyethyl)indole in 10 ml diethyl ether. After stirring 10 minutes a solution of 1.37 ml methyl iodide in 1.5 ml diethyl ether is added in one portion. The mixture is stirred for 15 minutes and then the ammonia is allowed to evaporate. The residue is mixed with 100 ml water and is extracted into 200 ml diethyl ether. The organic phase is separated and is dried over magnesium sulfate. Filtration and evaporation affords 3.64 g of 1-methyl-3-(2-hydroxyethyl)indole, an oil.

Workup

  1. additionis added in one portion
  2. customto evaporate
  3. additionThe residue is mixed with 100 ml water
  4. extractionis extracted into 200 ml diethyl ether
  5. customThe organic phase is separated
  6. dry with materialis dried over magnesium sulfate
  7. filtrationFiltration and evaporation

Sources & evidence

ORD record
ord-d961c34e52ac4a0fbaf51ea4925b98b8
Source dataset
uspto-grants-1981_03
Patent number
US04255432

Linked notes

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