4-Iodoanisole → HCID 21563763, compound

HRID 1580716Notes

Reaction equation

HRID 1580716 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:11]([CH2:18][C:19](=[O:21])[CH3:20])=[CH:10]2)=[CH:5][CH:4]=1.COC1C=CC(I)=CC=1.[H][H]>C(O)C.[Ni].C(O)(=O)C.C(OCC)C>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:11]([CH2:18][CH:19]([OH:21])[CH3:20])=[CH:10]2)=[CH:5][CH:4]=1

Participants

8

Reactant 3

HCID 696764-IodoanisoleHCID 21543496HCID 21543496, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 21563763HCID 21563763, compound

Reagents, catalysts & solvents 4

HCID 935NickelCatalystHCID 176Acetic AcidSolventHCID 702EthanolSolventHCID 3283Diethyl EtherSolvent

Procedure

5.6 G (0.02 mole) of 1-(4-methoxyphenyl)-3-(2-oxopropyl)indole, prepared as described in example 1 but using 4-methoxyiodobenzene instead of iodobenzene are dissolved in 50 ml of anhydrous ethanol in a 200 ml autoclave. 2 g of Raney nickel are added. The autoclave is brought to a pressure of 50 kg of hydrogen and heat is applied at 100° for 8 hours at this pressure. The reaction medium is taken to dryness and the residue dissolved in normal acetic acid in the presence of diethyl ether. The organic phase is dried and the solvents are removed. The residue is then distilled.

Workup

  1. temperatureheat
  2. customThe organic phase is dried
  3. customthe solvents are removed
  4. distillationThe residue is then distilled

Sources & evidence

ORD record
ord-420b040125554748a341356be1b92f7d
Source dataset
uspto-grants-1976_01
Patent number
US03933853

Reaction notes

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