5-Methoxyindole → 5-methoxy-2,3-dihydro-1H-indole

HRID 7420

Reaction equation

HRID 7420 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH:7]=[CH:6]2.C([BH3-])#N.[Na+]>C(O)(=O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH2:7][CH2:6]2

Participants

4

Reactant 2

HCID 138725-MethoxyindoleHCID 5003444Sodium cyanoborohydride

Product 1

HCID 107019745-methoxy-2,3-dihydro-1H-indoleYield 94%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of 5-methoxyindole (528 mg, 3.6 mmol) in acetic acid (5 mL) was added sodium cyanoborohydride (452 mg, 7.2 mmol) by small portions at room temperature and the mixture was stirred for 18 h in situ. The solvent was evaporated under reduced pressure and the obtained residue was dissolved in ethyl acetate. The organic layer was washed with saturated aqueous sodium hydrogencarbonate solution (×3) and saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure to give almost pure title compound (503 mg, 94%).

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. dissolutionthe obtained residue was dissolved in ethyl acetate
  3. washThe organic layer was washed with saturated aqueous sodium hydrogencarbonate solution (×3) and saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-246db8c799c144b3969777dadbb12e19
Source dataset
uspto-grants-2006_08
Patent number
US07087597B1

Linked notes

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