2-Iodotoluene → Indane-5-yl-p-tolylamine

HRID 1714716Notes

Reaction equation

HRID 1714716 reaction equation
[C:1]([NH:4][C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[CH2:10][CH2:9][CH2:8]2)(=O)[CH3:2].I[C:15]1[CH:20]=CC=[CH:17][C:16]=1[CH3:21].C(=O)([O-])[O-].[K+].[K+].[OH-].[K+]>O.[Cu].C(O)CC(C)C>[CH2:10]1[C:11]2[C:7](=[CH:6][C:5]([NH:4][C:1]3[CH:20]=[CH:15][C:16]([CH3:21])=[CH:17][CH:2]=3)=[CH:13][CH:12]=2)[CH2:8][CH2:9]1

Participants

8

Reactant 4

HCID 51282-IodotolueneHCID 11430Potassium CarbonateHCID 14797Potassium HydroxideHCID 583823N-(2,3-Dihydro-1H-inden-5-yl)acetamide

Product 1

HCID 15309875Indane-5-yl-p-tolylamineYield 96.4%

Reagents, catalysts & solvents 3

HCID 23978CopperCatalystHCID 962WaterSolvent2×HCID 31260Isoamyl AlcoholSolvent

Conditions

Temperature
200 °C

Procedure

5-(N-Acetylamino)indane (26.28 g (0.15 mol)), 43.61 g (0.20 mol) of iodotoluene, 25.88 g (0.188 mol) of anhydrous potassium carbonate and 2.38 g (0.038 mol) of copper powder were mixed, and heated up to 200° C. while introducing nitrogen gas, followed by stirring for 6 hours. After the termination of the reaction, cooling was conducted, and 22.3 g of potassium hydroxide dissolved in 20 ml of water and 50 ml of isoamyl alcohol were added to perform hydrolysis at 130° C. for 2 hours. After the termination of the hydrolysis, 250 ml of water was added, and isoamyl alcohol was removed by azeotropic distillation. Then, 200 ml of toluene was added to dissolve the reaction product. After filtration, dehydration was performed with magnesium sulfate. After magnesium sulfate was removed by filtration, the filtrate was concentrated, and purified by column chromatography (carrier: silica gel, eluent: toluene:hexane=1:4) to obtain 32.3 g of indane-5-yl-p-tolylamine.

Workup

  1. additionwhile introducing nitrogen gas
  2. customAfter the termination of the reaction
  3. temperaturecooling
  4. customhydrolysis at 130° C. for 2 hours
  5. additionwas added
  6. customisoamyl alcohol was removed by azeotropic distillation
  7. additionThen, 200 ml of toluene was added
  8. dissolutionto dissolve the reaction product
  9. filtrationAfter filtration, dehydration
  10. customAfter magnesium sulfate was removed by filtration
  11. concentrationthe filtrate was concentrated
  12. custompurified by column chromatography (carrier: silica gel, eluent: toluene:hexane=1:4)

Sources & evidence

ORD record
ord-a6db37ab49dd44b4813a92f0d43a214c
Source dataset
uspto-grants-2010_09
Patent number
US07799492B2

Reaction notes

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