Benzenepropanal → 3-Phenylmethyl-7-methoxyindole

HRID 51465

Reaction equation

HRID 51465 reaction equation
Cl.[CH3:2][O:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[NH:10]N.[C:12]1([CH2:18][CH2:19][CH:20]=O)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.P(Cl)(Cl)Cl.C(=O)(O)[O-].[Na+]>C1(C)C=CC=CC=1.O>[C:12]1([CH2:18][C:19]2[C:6]3[C:5](=[C:4]([O:3][CH3:2])[CH:9]=[CH:8][CH:7]=3)[NH:10][CH:20]=2)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

7

Reactant 4

HCID 7707BenzenepropanalHCID 24387Phosphorus trichlorideHCID 516892Sodium BicarbonateHCID 28494452-Methoxyphenylhydrazine Hydrochloride

Product 1

HCID 227407383-Phenylmethyl-7-methoxyindole

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

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)

Workup

  1. temperatureThe suspension was cooled
  2. customevaporated in vacuo
  3. dissolutionthe residue dissolved in 500 mL of dichloromethane
  4. washThe organic phase was washed with saturated sodium chloride
  5. dry with materialdried over sodium sulfate
  6. customevaporated in vacuo
  7. customThe residue was chromatographed on silica gel eluting with a gradient hexane/5-15% ethyl ether
  8. customto give product, 8.0 gm, 40%

Sources & evidence

ORD record
ord-e5b31f1a44974878a00a6afaac8c47d2
Source dataset
uspto-grants-2004_03
Patent number
US06713645B1

Linked notes

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