Sodium sulfate decahydrate → (5-Amino-1-methyl-1H-indol-2-yl)methanol

HRID 239900Notes

Reaction equation

HRID 239900 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH3:11])[C:6]([C:12](OCC)=[O:13])=[CH:5]2.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.O.O.O.O.O.O.O.O.O.S([O-])([O-])(=O)=O.[Na+].[Na+]>C1COCC1>[NH2:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH3:11])[C:6]([CH2:12][OH:13])=[CH:5]2

Participants

5

Reactant 3

HCID 62649Sodium sulfate decahydrateHCID 11424506Ethyl 5-amino-1-methyl-1H-indole-2-carboxylateHCID 21226445Aluminium lithium hydride

Product 1

HCID 45098216(5-Amino-1-methyl-1H-indol-2-yl)methanolYield 114.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of ethyl 5-amino-1-methyl-1H-indole-2-carboxylate (9.21 g) in THF (55 mL) was added dropwise to a solution of lithium aluminum hydride (2.08 g) in THF (110 mL) at 5° C., and the mixture was stirred at room temperature for 4.5 hr. To the reaction mixture was added sodium sulfate decahydrate (20.4 g), and the mixture was stirred at room temperature for 30 min. The insoluble material was filtered off and washed with THF. The filtrate was concentrated under reduced pressure to dryness to give the title compound (8.50 g, yield 100%) as a yellow solid.

Workup

  1. stirringthe mixture was stirred at room temperature for 30 min
  2. filtrationThe insoluble material was filtered off
  3. washwashed with THF
  4. concentrationThe filtrate was concentrated under reduced pressure to dryness

Sources & evidence

ORD record
ord-3571420a6ef14ba59b2e2d74bb5f0d10
Source dataset
uspto-grants-2014_02
Patent number
US08642770B2

Reaction notes

Loading…