Methanol → HCID 15411287, compound

HRID 848996Notes

Reaction equation

HRID 848996 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH2:11][O:12][C:13]1[CH:14]=[C:15]([CH:18]=[CH:19][CH:20]=1)[CH2:16]Cl.[C:21]([C:23]1[C:24](=[O:34])[NH:25][C:26]2[C:31]([CH:32]=1)=[CH:30][C:29]([OH:33])=[CH:28][CH:27]=2)#[N:22].C([O-])([O-])=O.[K+].[K+].CO>CN(C=O)C.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[C:21]([C:23]1[C:24](=[O:34])[NH:25][C:26]2[C:31]([CH:32]=1)=[CH:30][C:29]([O:33][CH2:16][C:15]1[CH:18]=[CH:19][CH:20]=[C:13]([O:12][CH2:11][C:2]3[CH:3]=[CH:4][C:5]4[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=4)[N:1]=3)[CH:14]=1)=[CH:28][CH:27]=2)#[N:22]

Participants

7

Reactant 4

HCID 887MethanolHCID 11430Potassium CarbonateHCID 145017062-(3-Chloromethylphenoxy)methylquinolineHCID 19369483HCID 19369483, compound

Product 1

HCID 15411287HCID 15411287, compoundYield 4.7%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 6228DimethylformamideSolvent

Procedure

3-(2-quinolinylmethoxy)benzyl chloride (3.49 g, 12.3 mmol) was added to a solution of 2.45 g (12.3 mmol) of 3-cyano-6-hydroxy-1,2-dihydroquinolin-2-one in 100 ml of DMF, followed by the further addition of 2.04 g (14.8 mmol) of K2CO3 and 396 mg (1.23 mmol) of tetra-n-butylammonium bromide. The resulting mixture was stirred under an argon gas stream at room temperature for 24 hours. The reaction mixture was concentrated under reduced pressure, followed by the addition of CHCl3 --MeOH and water to extract the reaction product into the organic layer. The organic layer was dried over Na2SO4 and then concentrated under reduced pressure. The residue was subjected to chromatography on a silica gel column. Subsequent to elution with CHCl3, recrystallization was conducted from a CHCl3 --MeOH mixed solvent, whereby 250 mg of the title compound were obtained as yellow powder (yield: 4.7%). Melting point: 145-147° C. (decomposed).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additionfollowed by the addition of CHCl3
  3. extractionMeOH and water to extract the reaction product into the organic layer
  4. dry with materialThe organic layer was dried over Na2SO4
  5. concentrationconcentrated under reduced pressure
  6. washSubsequent to elution
  7. customwith CHCl3, recrystallization

Sources & evidence

ORD record
ord-b16e660adbcc47498951d93f1e53f095
Source dataset
uspto-grants-2000_01
Patent number
US06011033

Reaction notes

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