Sodium Hydroxide → 2-Aminomethylindoline

HRID 52465Notes

Reaction equation

HRID 52465 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[C:7]([CH:10]1[CH2:18][C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[NH:11]1)(=O)[NH2:8].[OH-].[Na+]>C1COCC1>[NH2:8][CH2:7][CH:10]1[CH2:18][C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[NH:11]1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 139378102,3-Dihydro-1H-indole-2-carboxamideHCID 21226445Aluminium lithium hydride2×

Product 1

HCID 218304062-AminomethylindolineYield 90%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

To a suspension of LiAlH4 (6.0 g, 0.157 mol) in THF (200 mL) was added dropwise a suspension of 2-carbamoylindoline (17.0 g, 0.105 mol) in THF (700 mL) over 50 min. The mixture was refluxed for 5 h and then LiAlH4 (6.0 g) was added further. The reflux was continued additionally for 6 h and the mixture was treated with 10% aqueous THF after being cooled with ice bath. Aqueous 1N NaOH was added and the mixture was extracted with a mixture of diethyl ether and THF. The organic layer was washed with water and brine, dried over magnesium sulfate, and concentrated to give 13.91 g of 2-aminomethylindoline (90%): 1H NMR (270 MHz, CDCl3) δ7.11 (dd, 1H, J=7, 1 Hz), 7.01 (dt, 1H, J=1, 7 Hz), 6.68 (dt, 1H, J=1, 7 Hz), 6.61 (d, 1H, J=7 Hz), 3.84 (m, 1H), 3.11 (dd, 1H, J=16, 9 Hz), 2.86 (dd, 1H, J=13, 5 Hz), 2.70 (m, 2H).

Workup

  1. additionwas added dropwise
  2. temperatureThe mixture was refluxed for 5 h
  3. temperatureafter being cooled with ice bath
  4. extractionthe mixture was extracted with a mixture of diethyl ether and THF
  5. washThe organic layer was washed with water and brine
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-d4385e4a55aa4261a411d22e6f552ffe
Source dataset
uspto-grants-1997_04
Patent number
US05616586

Reaction notes

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