Toluene → HCID 68749464, compound

HRID 228351Notes

Reaction equation

HRID 228351 reaction equation
[CH3:1][C:2]([C:4]1[CH:5]=[CH:6][C:7]([OH:10])=[CH:8][CH:9]=1)=[O:3].Cl[C:12]1[CH:20]=[CH:19][C:15]([C:16]([NH2:18])=[O:17])=[CH:14][N:13]=1.C([O-])([O-])=O.[K+].[K+].C1(C)C=CC=CC=1>CN(C=O)C>[C:2]([C:4]1[CH:9]=[CH:8][C:7]([O:10][C:14]2[N:13]=[CH:12][CH:20]=[CH:19][C:15]=2[C:16]([NH2:18])=[O:17])=[CH:6][CH:5]=1)(=[O:3])[CH3:1]

Participants

6

Reactant 4

HCID 1140TolueneHCID 74694'-HydroxyacetophenoneHCID 11430Potassium CarbonateHCID 804566-Chloronicotinamide

Product 1

HCID 68749464HCID 68749464, compoundYield 20%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-Hydroxyacetophenone (1 equiv), 6-chloronicotinamide (1 equiv) and K2CO3 (1.4 equiv) in anhydrous DMF (0.4 M) was heated at 150° C. under nitrogen during 2.5 days. After cooling down to room temperature, toluene was added and solvents were evaporated. The residue was partitioned in water/EtOAc. The aqueous layer was thoroughly extracted with EtOAc. The combined organic layer was dried over Na2SO4, filtered and concentrated under vacuum (toluene was added to aid DMF evaporation). The crude mixture was purified by flash chromatography using EtOAc/CH2Cl2/2 M NH3 in MeOH (12:7:1) as eluent in 20% yield.

Workup

  1. customsolvents were evaporated
  2. customThe residue was partitioned in water/EtOAc
  3. extractionThe aqueous layer was thoroughly extracted with EtOAc
  4. dry with materialThe combined organic layer was dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum (toluene was added to aid DMF evaporation)
  7. customThe crude mixture was purified by flash chromatography

Sources & evidence

ORD record
ord-fe7856706bb3400e8334df79fe861ed9
Source dataset
uspto-grants-2009_07
Patent number
US07560463B2

Reaction notes

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