2,3-Dihydro-1H-indole-2-carboxamide → 2-Aminomethylindoline

HRID 1601076Notes

Reaction equation

HRID 1601076 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[NH:7]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH2:9][CH:8]1[C:16]([NH2:18])=O>C1COCC1>[NH2:18][CH2:16][CH:8]1[CH2:9][C:10]2[C:15](=[CH:14][CH:13]=[CH:12][CH:11]=2)[NH:7]1

Participants

4

Reactant 2

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

Product 1

HCID 218304062-AminomethylindolineYield 51%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

LAH (20 mL, 1M solution in THF) was added dropwise through a syringe to a solution of (±)-indoline-2-carboxamide (2.2 g, 13.6 mmol) in anhydrous THF (20 mL) with cooling, and the resulting solution was refluxed under argon for 5 h. More LAH (20 mL) was added, and reflux was continued for another 6 h. 10% aqueous THF was added dropwise with cooling to destroy excess LAH, and then Et2O was added. After stirring for 10 min, the colorless precipitate was removed by filtration and washed with THF. The filtrate was dried (K2CO3), concentrated, and purified by silica gel flash chromatography (90:10:0.2 CH2Cl2 /MeOH/Et3N). The title compound (1.02 g, 51%) was obtained as an amber oil: MS (ES) m/e 149.0 (M+H)+.

Workup

  1. temperaturewith cooling
  2. temperaturethe resulting solution was refluxed under argon for 5 h
  3. temperaturereflux
  4. temperaturewith cooling
  5. customto destroy excess LAH
  6. additionEt2O was added
  7. customthe colorless precipitate was removed by filtration
  8. washwashed with THF
  9. dry with materialThe filtrate was dried (K2CO3)
  10. concentrationconcentrated
  11. custompurified by silica gel flash chromatography (90:10:0.2 CH2Cl2 /MeOH/Et3N)

Sources & evidence

ORD record
ord-1f0214d779e84795af0f569e1d3eee14
Source dataset
uspto-grants-1999_11
Patent number
US05977101

Reaction notes

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