Potassium Carbonate → Indane-5-yl-p-tolylamine

HRID 2405626Notes

Reaction equation

HRID 2405626 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].IC1C=[CH:19][C:18]([CH3:21])=[CH:17][CH:16]=1.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:16]=[CH:17][C:18]([CH3:21])=[CH:19][CH:2]=3)=[CH:13][CH:12]=2)[CH2:8][CH2:9]1

Participants

8

Reactant 4

HCID 11430Potassium CarbonateHCID 122074-IodotolueneHCID 14797Potassium HydroxideHCID 583823N-(2,3-Dihydro-1H-inden-5-yl)acetamide

Product 1

HCID 15309875Indane-5-yl-p-tolylamine

Reagents, catalysts & solvents 3

HCID 23978CopperCatalystHCID 962WaterSolvent2×HCID 31260Isoamyl AlcoholSolvent

Conditions

Temperature
20 °C

Procedure

26.28 g (0.15 mol) of 5-(N-acetylamino)indane, 43.61 g (0.20 mol) of p-Iodotoluene, 25.88 g (0.188 mol) of anhydrous potassium carbonate and 2.38 g (0.038 mol) of a copper powder were mixed and while introducing a nitrogen gas, the resulting mixture was heated to 20° C. and stirred for 6 hours. After completion of the reaction, 22.3 g of potassium hydroxide dissolved in 20 ml of water and 50 ml of isoamyl alcohol were added to conduct hydrolysis at 130° C. for 2 hours. After completion of the hydrolysis, 250 ml of water was added, and Isoamyl alcohol was removed by azeotropic distillation. 200 ml of toluene was added to dissolve the reaction product. After filtration, the reaction product was dehydrated with magnesium sulfate. After filtering out the magnesium sulfate, the filtrate was concentrated, and purified with column chromatography (carrier: silica gel, elute: toluene:hexane=1:4) to obtain 32.3 of indan-5-yl-p-tolylamine.

Workup

  1. additionwhile introducing a nitrogen gas
  2. customhydrolysis at 130° C. for 2 hours
  3. additionwas added
  4. customIsoamyl alcohol was removed by azeotropic distillation
  5. addition200 ml of toluene was added
  6. dissolutionto dissolve the reaction product
  7. filtrationAfter filtration
  8. filtrationAfter filtering out the magnesium sulfate
  9. concentrationthe filtrate was concentrated
  10. custompurified with column chromatography (carrier: silica gel, elute: toluene:hexane=1:4)

Sources & evidence

ORD record
ord-1be0256166954d3992027ba574ff1c4c
Source dataset
uspto-grants-2014_08
Patent number
US08808951B2

Reaction notes

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