Reaction #79743

Reaction equation

2-methoxyphenylhydrazine hydrochloride

3-phenylpropionaldehyde

sodium bicarbonate

phosphorous trichloride

→

3-phenylmethyl-7-methoxyindole

Solvents

water

toluene

Conditions

Workup

1. 1
   TemperatureThe suspension was cooled
2. 2
   Otherevaporated in vacuo
3. 3
   workup.DISSOLUTIONthe residue dissolved in 500 mL of dichloromethane
4. 4
   WashThe organic phase was washed with saturated sodium chloride
5. 5
   Dryingdried over sodium sulfate
6. 6
   Otherevaporated in vacuo
7. 7
   OtherThe residue was chromatographed on silica gel eluting with a gradient hexane/5-15% ethyl ether
8. 8
   Otherto give product, 8.0 gm, 40%

Procedure

A mixture of 15 gm (0.086 mol) of 2-methoxyphenylhydrazine hydrochloride and 12 mL (0.09 mol) of 3-phenylpropionaldehyde in 300 mL of toluene was refluxed for 1.5 hours with azeotropic removal of water. The suspension was cooled, evaporated in vacuo and the residue dissolved in 500 mL of dichloromethane and stirred with 9 mL (0.09 mol) of phosphorous trichloride for 18 hours. The solution was poured into ice-water, stirred well, and made basic with sodium bicarbonate. The organic phase was washed with saturated sodium chloride, dried over sodium sulfate, and evaporated in vacuo. The residue was chromatographed on silica gel eluting with a gradient hexane/5-15% ethyl ether to give product, 8.0 gm, 40%, as a viscous oil. 1H NMR (CDCl3) δ: 3.95 (s, 3H), 4.10 (s, 2H), 6.65 (d, 1H), 6.90 (s, 1H), 7.00 (t, 1H), 7.10 (d, 1H), 7.20 (m, 1H), 7.30 (m, 4H), 8.20 (br s, 1H)

Source