1-Amino-2-propanol → 3-Methyl-6-(2-methylphenyl)-4,5,6,7-tetrahydroindol-4-one

HRID 1700430Notes

Reaction equation

HRID 1700430 reaction equation
[C:1]1([CH:7]2[CH2:12][C:11](=O)[CH2:10][C:9](=[O:14])[CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH2:15][CH2:16][CH:17](O)[CH3:18].O1CCC[CH2:21]1>>[CH3:18][C:17]1[C:10]2[C:9](=[O:14])[CH2:8][CH:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][C:6]=3[CH3:21])[CH2:12][C:11]=2[NH:15][CH:16]=1

Participants

4

Reactant 3

HCID 41-Amino-2-propanolHCID 8028TetrahydrofuranHCID 5689621,3-Cyclohexanedione, 5-phenyl-

Product 1

HCID 111074403-Methyl-6-(2-methylphenyl)-4,5,6,7-tetrahydroindol-4-one

Conditions

Temperature
150 °C

Procedure

A mixture of 5-phenylcyclohexane-1,3-dione (2.0 g), 3-aminopropan-2-ol (0.97 g), molecular sieves 4A (12 g) and tetrahydrofuran (30 ml) was refluxed for 12 hours and cooled, and insoluble materials were filtered off. Under reduced pressure, the solvent was evaporated, and the residue was dissolved in dimethylformamide (40 ml). To the mixture were added 2-bromomesitylene (2.0 g), tetrakistriphenylphosphine palladium (0.29 g) and potassium carbonate (2.7 g), and the mixture was stirred at 150° C. for 5 hours and concentrated under reduced pressure. The residue was dissolved in ethyl acetate, and the solution was washed with sodium hydrogen carbonate solution, water and saturated brine, dried with magnesium sulfate and concentrated under reduced pressure. The residue was recrystallized from ethyl acetate-hexane to give colorless crystals of 3-methyl-6-(2-methylphenyl)-4,5,6,7-tetrahydroindol-4-one (1.1 g).

Workup

  1. temperaturewas refluxed for 12 hours
  2. temperaturecooled
  3. filtrationinsoluble materials were filtered off
  4. customUnder reduced pressure, the solvent was evaporated
  5. dissolutionthe residue was dissolved in dimethylformamide (40 ml)
  6. additionTo the mixture were added 2-bromomesitylene (2.0 g), tetrakistriphenylphosphine palladium (0.29 g) and potassium carbonate (2.7 g)
  7. concentrationconcentrated under reduced pressure
  8. dissolutionThe residue was dissolved in ethyl acetate
  9. washthe solution was washed with sodium hydrogen carbonate solution, water and saturated brine
  10. dry with materialdried with magnesium sulfate
  11. concentrationconcentrated under reduced pressure
  12. customThe residue was recrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-792fe49068e84f7b86d04dedfffa125c
Source dataset
uspto-grants-2002_02
Patent number
US06350749B1

Reaction notes

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