Indene → 4-(1H-Inden-2-yl)aniline

HRID 650309Notes

Reaction equation

HRID 650309 reaction equation
[CH2:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.[NH2:10][C:11]1[CH:16]=[CH:15][C:14](I)=[CH:13][CH:12]=1>CC([O-])=O.CC([O-])=O.[Pd+2].C(N(CC)CC)C>[NH2:10][C:11]1[CH:16]=[CH:15][C:14]([C:2]2[CH2:3][C:4]3[C:9]([CH:1]=2)=[CH:8][CH:7]=[CH:6][CH:5]=3)=[CH:13][CH:12]=1

Participants

5

Reactant 2

HCID 7219IndeneHCID 108934-Iodoaniline

Product 1

HCID 217149554-(1H-Inden-2-yl)aniline

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 8471TriethylamineSolvent

Procedure

20 ml of triethylamine, 2.2 g (20 mmol) of indene, 4.38 g (20 mmol) of para-amino-iodo-benzene and 0.134 g (0.6 mmol) of Pd(OAc)2 were stirred under reflux for 10 h. After that all triethylamine was removed under reduced pressure. The residue was treated with 80 ml of 15% HCl. Forming precipitate was separated and washed with dichloromethane. The resulting substance was treated with the mixture 50 ml of dichloromethane and 50 ml of 5% KOH in water. Organic layer was separated, washed twice with water, filtered and dried over Na2SO4. Dichloromethane was removed and the residue was recrystallized from 20 ml of EtOH. The yield of product was 21%.

Workup

  1. temperatureunder reflux for 10 h
  2. customAfter that all triethylamine was removed under reduced pressure
  3. additionThe residue was treated with 80 ml of 15% HCl
  4. customForming precipitate
  5. customwas separated
  6. washwashed with dichloromethane
  7. additionThe resulting substance was treated with the mixture 50 ml of dichloromethane and 50 ml of 5% KOH in water
  8. customOrganic layer was separated
  9. washwashed twice with water
  10. filtrationfiltered
  11. dry with materialdried over Na2SO4
  12. customDichloromethane was removed
  13. customthe residue was recrystallized from 20 ml of EtOH

Sources & evidence

ORD record
ord-c008d2c1833d47bba2fa66c6096c6460
Source dataset
uspto-grants-2001_08
Patent number
US06271411B1

Reaction notes

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