Dimethylformamide → HCID 70873472, compound

HRID 2172213Notes

Reaction equation

HRID 2172213 reaction equation
[CH3:1][CH2:2][O:3][C:4]([C:6]1[CH:11]=[CH:10][C:9](Cl)=[N:8][CH:7]=1)=[O:5].[F:13][C:14]([F:24])([F:23])[O:15][C:16]1[CH:21]=[CH:20][C:19]([OH:22])=[CH:18][CH:17]=1.C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>O>[CH2:2]([O:3][C:4](=[O:5])[C:6]1[CH:11]=[CH:10][C:9]([O:22][C:19]2[CH:20]=[CH:21][C:16]([O:15][C:14]([F:13])([F:23])[F:24])=[CH:17][CH:18]=2)=[N:8][CH:7]=1)[CH3:1]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 70015p-(Trifluoromethoxy)phenolHCID 2799611Ethyl 6-chloronicotinate

Product 1

HCID 70873472HCID 70873472, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
105 °C

Procedure

Ethyl 6-chloro nicotinate (5.00 g, 26.9 mmol), 4-(trifluoromethoxy)phenol (5.28 g, 29.6 mmol), potassium carbonate (4.84 g, 35.0 mmol) and N,N-dimethylformamide (50 ml) were mixed and stirred at 100 to 110° C. overnight. The reaction mixture was poured into water, followed by extraction with ethyl acetate. The organic layer was washed with a saturated sodium chloride aqueous solution and dried over magnesium sulfate. The organic layer was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=100:0→70:30) to afford the title compound as a colorless oil (7.48 g, 85%).

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe organic layer was washed with a saturated sodium chloride aqueous solution
  3. dry with materialdried over magnesium sulfate
  4. concentrationThe organic layer was concentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=100:0→70:30)

Sources & evidence

ORD record
ord-450a4bc4a61743d8b2817af120335fa0
Source dataset
uspto-grants-2015_06
Patent number
US09051333B2

Reaction notes

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