Aluminium lithium hydride → N-methyl(3-vinyl-1H-indol-2-yl)methanamine

HRID 2097182Notes

Reaction equation

HRID 2097182 reaction equation
[CH3:1][NH:2][C:3]([C:5]1[NH:6][C:7]2[C:12]([C:13]=1[CH:14]=[CH2:15])=[CH:11][CH:10]=[CH:9][CH:8]=2)=O.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCOCC1>[CH3:1][NH:2][CH2:3][C:5]1[NH:6][C:7]2[C:12]([C:13]=1[CH:14]=[CH2:15])=[CH:11][CH:10]=[CH:9][CH:8]=2

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 59277607N-methyl-3-vinyl-1H-indole-2-carboxamide

Product 1

HCID 59277599N-methyl(3-vinyl-1H-indol-2-yl)methanamineYield 62.4%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

A solution of N-methyl-3-vinyl-1H-indole-2-carboxamide (740 mg, 3.7 mmol) in dioxane was added slowly to an ice-cooled solution of lithium aluminium hydride (2.1 g, 55.5 mmol) in dioxane (100 mL). The mixture was stirred at reflux overnight. Excess lithium aluminium hydride was quenched with 15% NaOH (10 mL) and the mixture separated. The aqueous phase was washed twice with ethyl acetate and the combined organic phases dried to afford the title compound (430 mg 61%). 1H NMR (400 MHz, DMSO-d6) δ 11.09 (s, 1H), 7.75 (d, J=8 Hz, 1H), 7.49 (d, J=6.4 Hz, 1H), 7.09-7.05 (m, 2H), 7.04-6.90 (m, 1H), 5.54 (d, J=16 Hz, 1H), 5.06 (d, J=10.0 Hz, 1H), 3.84 (s, 2H), 2.27 (s, 3H).

Workup

  1. temperatureat reflux overnight
  2. customExcess lithium aluminium hydride was quenched with 15% NaOH (10 mL)
  3. customthe mixture separated
  4. washThe aqueous phase was washed twice with ethyl acetate
  5. customthe combined organic phases dried

Sources & evidence

ORD record
ord-261b8dc2cff1427bb43386981d2e4b0a
Source dataset
uspto-grants-2013_05
Patent number
US08450307B2

Reaction notes

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