4-Iodophenol → 6-(4-Iodo-phenoxy)-nicotinamide

HRID 492355Notes

Reaction equation

HRID 492355 reaction equation
[I:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.Cl[C:10]1[CH:18]=[CH:17][C:13]([C:14]([NH2:16])=[O:15])=[CH:12][N:11]=1.C(=O)([O-])[O-].[K+].[K+].CC(N(C)C)=O>O>[I:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:10]2[CH:18]=[CH:17][C:13]([C:14]([NH2:16])=[O:15])=[CH:12][N:11]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 108944-IodophenolHCID 11430Potassium CarbonateHCID 31374DimethylacetamideHCID 804566-Chloronicotinamide

Product 1

HCID 597303076-(4-Iodo-phenoxy)-nicotinamideYield 85%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
200 °C

Procedure

Combine 4-iodophenol (6.31 g, 28.7 mmol), 6-chloro-nicotinamide (4.51 g, 28.8 mmol), potassium carbonate (10.0 g, 72.4 mmol), and dimethylacetamide (145 mL), stir and heat at 200° C. After 3 h. cool to ambient temperature and dilute with water (600 mL), filter, and dry in vacuo to provide 8.27 g (85%) of the title compound as a white/brown solid: mass spectrum (electrospray): m/z=341.0 (M+1); 1H NMR (methanol-d4): 8.67 (d, 1H, J=2.4 Hz), 8.31 (dd, 1H, J=2.4, 8.3 Hz), 7.82-7.79 (m, 2H), 7.09 (d, 1H, J=8.8 Hz), 7.03-6.99 (m, 2H).

Workup

  1. temperatureAfter 3 h. cool to ambient temperature
  2. filtrationfilter
  3. customdry in vacuo

Sources & evidence

ORD record
ord-adebe402d912425382663df3b6c375b0
Source dataset
uspto-grants-2009_05
Patent number
US07531557B2

Reaction notes

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