4-Methoxybenzylamine → HCID 66700157, compound

HRID 1910714Notes

Reaction equation

HRID 1910714 reaction equation
Cl[C:2]1[C:7]([C:8](=[O:12])[CH:9]=[CH:10][CH3:11])=[CH:6][CH:5]=[CH:4][N:3]=1.ClC1C(C(=O)CC=C)=CC=CN=1.[CH3:25][O:26][C:27]1[CH:34]=[CH:33][C:30]([CH2:31][NH2:32])=[CH:29][CH:28]=1>C(O)C>[CH3:25][O:26][C:27]1[CH:34]=[CH:33][C:30]([CH2:31][N:32]2[C:2]3[C:7](=[CH:6][CH:5]=[CH:4][N:3]=3)[C:8](=[O:12])[CH2:9][CH:10]2[CH3:11])=[CH:29][CH:28]=1

Participants

5

Reactant 3

HCID 754524-MethoxybenzylamineHCID 78128433HCID 78128433, compoundHCID 86664527HCID 86664527, compound

Product 1

HCID 66700157HCID 66700157, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
70 °C

Procedure

[Step 3] 2.2 g of the mixture of 1-(2-chloropyridin-3-yl)but-2-en-1-one and 1-(2-chloropyridin-3-yl)but-3-en-1-one and 4-methoxybenzylamine were dissolved in 30 mL of ethanol and stirred overnight at 70° C. Following completion of the reaction, the solution was concentrated under reduced pressure and water was added to the resulting residue followed by extracting three times with chloroform. After washing with saturated brine and dehydrating with anhydrous sodium sulfate, the solution was concentrated under reduced pressure and the resulting residue was purified using silica gel chromatography (ethyl acetate:hexane=1:3) to obtain 2.7 g of 1-(4-methoxybenzyl)-4-oxo-2-methyl-2,3-dihydro-1H-[1,8]-naphthyridine in the form of a yellow oil (80%).

Workup

  1. customcompletion of the reaction
  2. concentrationthe solution was concentrated under reduced pressure and water
  3. additionwas added to the resulting residue
  4. extractionby extracting three times with chloroform
  5. washAfter washing with saturated brine
  6. concentrationthe solution was concentrated under reduced pressure
  7. customthe resulting residue was purified

Sources & evidence

ORD record
ord-72470637a7fe4d428f339b7a1dfbd1c0
Source dataset
uspto-grants-2013_12
Patent number
US08604030B2

Reaction notes

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