Indene → 2-(4-Acetamido-phenyl)-indene

HRID 650310

Reaction equation

HRID 650310 reaction equation
[CH2:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.[NH:10]([C:14]1[CH:19]=[CH:18][C:17](I)=[CH:16][CH:15]=1)[C:11]([CH3:13])=[O:12]>CC([O-])=O.CC([O-])=O.[Pd+2].C(N(CC)CC)C>[C:11]([NH:10][C:14]1[CH:19]=[CH:18][C:17]([C:2]2[CH2:3][C:4]3[C:9]([CH:1]=2)=[CH:8][CH:7]=[CH:6][CH:5]=3)=[CH:16][CH:15]=1)(=[O:12])[CH3:13]

Participants

5

Reactant 2

HCID 7219IndeneHCID 12147N-(4-Iodophenyl)acetamide

Product 1

HCID 113796782-(4-Acetamido-phenyl)-indene

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 8471TriethylamineSolvent

Procedure

20 ml of triethylamine, 2.2 g (20 mmol) of indene, 5.22 , (20 mmol) of para-acetamino-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 the mixture 50 ml of dichloromethane and 50 ml of 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 13%.

Workup

  1. temperatureunder reflux for 10 h
  2. customAfter that all triethylamine was removed under reduced pressure
  3. additionThe residue was treated with the mixture 50 ml of dichloromethane and 50 ml of water
  4. customOrganic layer was separated
  5. washwashed twice with water
  6. filtrationfiltered
  7. dry with materialdried over Na2SO4
  8. customDichloromethane was removed
  9. customthe residue was recrystallized from 20 ml of EtOH

Sources & evidence

ORD record
ord-af00d3d8084748f690d1c0ee0b436d4f
Source dataset
uspto-grants-2001_08
Patent number
US06271411B1

Linked notes

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