1-Methyl-1H-indole-6-carbonitrile → 1-(1-Methyl-1H-indol-6-yl)methanamine

HRID 2041225Notes

Reaction equation

HRID 2041225 reaction equation
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:11]#[N:12])[CH:9]=2)[CH:4]=[CH:3]1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[NH2:12][CH2:11][C:8]1[CH:9]=[C:10]2[C:5]([CH:4]=[CH:3][N:2]2[CH3:1])=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 153844931-Methyl-1H-indole-6-carbonitrileHCID 21226445Aluminium lithium hydride

Product 1

HCID 185257681-(1-Methyl-1H-indol-6-yl)methanamineYield 91%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
50 °C

Procedure

Dissolve 1-methylindole-6-carbonitrile (0.97 g, 6.18 mmol) in anhydrous THF (10 mL) and add slowly to 1M lithium aluminum hydride in THF (1.24 mL, 1.24 mmol) at ambient temperature. Heat the reaction mixture at 50° C. for 17 h and cool to ambient temperature. Quench the reaction mixture with water until a granular precipitate starts to form and filter through a pad of Celite®. Evaporate the solvent and purify by SCX chromatography to obtain the title compound as a yellow oil (0.9 g, 91%). GC-MS m/z: 160 (M+).

Workup

  1. temperaturecool to ambient temperature
  2. customQuench the reaction mixture with water until a granular precipitate
  3. customto form
  4. filtrationfilter through a pad of Celite®
  5. customEvaporate the solvent
  6. custompurify by SCX chromatography

Sources & evidence

ORD record
ord-7ab42e5c300f40a58c839a92ad7eaa40
Source dataset
uspto-grants-2013_11
Patent number
US08580780B2

Reaction notes

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