Sodium Hydroxide → 7-Methyl-2,3-dihydro-1H-indole

HRID 1275647Notes

Reaction equation

HRID 1275647 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:10]=1[NH:9][CH:8]=[CH:7]2.C([BH3-])#N.[Na+].[OH-].[Na+]>C(O)(=O)C.O>[CH3:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:10]=1[NH:9][CH2:8][CH2:7]2

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 702757-MethylindoleHCID 5003444Sodium cyanoborohydride

Product 1

HCID 123777887-Methyl-2,3-dihydro-1H-indoleYield 111.5%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

To a stirred solution of 7-methylindole (10.27 g, 78.3 mmol) in glacial acetic acid (50 mL) is added sodium cyanoborohydride (6.33 g, 100.7 mmol) portionwise over a 5 minute period. The reaction solution is allowed to stir for 1 hour. The solution is diluted with water (500 mL) and basified with 50% sodium hydroxide solution. The basic solution is extracted with three 250 mL portions of diethyl ether. The organic fractions are combined, dried over anhydrous potassium carbonate, filtered and evaporated to give a pink oil. The oil is purified by silica gel column chromatography using 20% ethyl acetate/hexanes as eluent to give 11.63 g of 2,3-dihydro-7-methylindole as a colorless oil (94% yield).

Workup

  1. extractionThe basic solution is extracted with three 250 mL portions of diethyl ether
  2. dry with materialdried over anhydrous potassium carbonate
  3. filtrationfiltered
  4. customevaporated
  5. customto give a pink oil
  6. customThe oil is purified by silica gel column chromatography

Sources & evidence

ORD record
ord-6311792080f14d9093bb90b63962aede
Source dataset
uspto-grants-2000_12
Patent number
US06162818

Reaction notes

Loading…