Hydrochloric Acid → HCID 21714958, compound

HRID 650312Notes

Reaction equation

HRID 650312 reaction equation
CN(C=O)C.[CH2:6]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:8]=[CH:7]1.[NH2:15][C:16]1[CH:21]=[CH:20][C:19](I)=[CH:18][CH:17]=1.Cl>CC([O-])=O.CC([O-])=O.[Pd+2].C(N(CC)CC)C>[NH2:15][C:16]1[CH:21]=[CH:20][C:19]([CH:6]2[C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[CH:8]=[CH:7]2)=[CH:18][CH:17]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6228DimethylformamideHCID 7219IndeneHCID 108934-Iodoaniline

Product 1

HCID 21714958HCID 21714958, compound

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 8471TriethylamineSolvent

Procedure

20 ml of DMF, 2.2 g (20 mmol) of indene, 4,4 g (20 mmol) of para-amino-iodo-benzene, 2 ml of triethylamine and 0,134 (0,6 mmol) of Pd(OAc)2 were stirred under reflux for 10 h. The resulting mixture was poured into 200 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 yeld of product was 70%.

Workup

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

Sources & evidence

ORD record
ord-6abd163cd21249c8b233fae6e35a7e42
Source dataset
uspto-grants-2001_08
Patent number
US06271411B1

Reaction notes

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