4-Methyloxybenzyl chloride → HCID 117770821, compound

HRID 1526395Notes

Reaction equation

HRID 1526395 reaction equation
[I:1][C:2]1[C:3]([O:11][CH3:12])=[C:4]([C:9]#[N:10])[C:5](=[O:8])[NH:6][CH:7]=1.[CH3:13][O:14][C:15]1[CH:22]=[CH:21][C:18]([CH2:19]Cl)=[CH:17][CH:16]=1>[Ag-]=O.C1(C)C=CC=CC=1>[I:1][C:2]1[CH:7]=[N:6][C:5]([O:8][CH2:19][C:18]2[CH:21]=[CH:22][C:15]([O:14][CH3:13])=[CH:16][CH:17]=2)=[C:4]([C:3]=1[O:11][CH3:12])[C:9]#[N:10]

Participants

5

Reactant 2

HCID 699934-Methyloxybenzyl chloride2×HCID 66815465HCID 66815465, compound

Product 1

HCID 117770821HCID 117770821, compoundYield 77.1%

Reagents, catalysts & solvents 2

HCID 178418778HCID 178418778, compoundCatalystHCID 1140TolueneSolvent

Conditions

Temperature
110 °C

Procedure

To a mixture of 5-iodo-4-methoxy-2-oxo-1,2-dihydropyridine-3-carbonitrile obtained in Step A (3.00 g), silver(I) oxide (2.77 g) and toluene (80 mL) was added 4-methoxybenzyl chloride (2.21 g) at room temperature, and the mixture was stirred 110° C. for 5 hr. To the reaction mixture was added 4-methoxybenzyl chloride (2.21 g), and the mixture was stirred at 110° C. for 16 hr. The reaction mixture was cooled to room temperature, the insoluble substance was removed by filtration, and the filtrate was concentrated under reduced pressure. To the residue was added diethyl ether, and the precipitate was collected by filtration to give the title compound (3.32 g).

Workup

  1. stirringthe mixture was stirred at 110° C. for 16 hr
  2. temperatureThe reaction mixture was cooled to room temperature
  3. customthe insoluble substance was removed by filtration
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. additionTo the residue was added diethyl ether
  6. filtrationthe precipitate was collected by filtration

Sources & evidence

ORD record
ord-05be1c7c85ca4245a7e20c3d3bce9da8
Source dataset
uspto-grants-2015_07
Patent number
US09085578B2

Reaction notes

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