Potassium Carbonate → HCID 15411289, compound

HRID 848997Notes

Reaction equation

HRID 848997 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:20]=[CH:19][C:16]([CH2:17]Cl)=[CH:15][CH:14]=1.[CH3:21][C:22]1([CH3:33])[C:30]2[C:25](=[CH:26][CH:27]=[C:28]([OH:31])[CH:29]=2)[NH:24][C:23]1=[O:32].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[CH3:21][C:22]1([CH3:33])[C:30]2[C:25](=[CH:26][CH:27]=[C:28]([O:31][CH2:17][C:16]3[CH:19]=[CH:20][C:13]([O:12][CH2:11][C:2]4[CH:3]=[CH:4][C:5]5[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=5)[N:1]=4)=[CH:14][CH:15]=3)[CH:29]=2)[NH:24][C:23]1=[O:32]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 12016525-Hydroxy-3,3-dimethylindolin-2-oneHCID 147741632-(4-Chloromethylphenoxy)methylquinoline

Product 1

HCID 15411289HCID 15411289, compound

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 6228DimethylformamideSolvent

Procedure

4-(2-Quinolinylmethoxy)benzyl chloride (567 mg, 2 was dissolved in 20 ml of DMF, followed by the addition of 354 mg (2 mmol) of 3,3-dimethyl-5-hydroxy-2,3-dihydro-1H-indol-2-one, 64 mg (0.2 mmol) of tetra-n-butylammonium bromide and 691 mg (5 mmol) of K2CO3. The resultant mixture was stirred under an argon gas stream at 50° C. for 72 hours. After the solvent was distilled off, water was added, and the thus-formed mixture was extracted twice in a CHCl3 --MeOH (3:1) mixed solvent. The extract was dried over MgSO4 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 AcOEt-hexane, whereby 199 mg of the title compound were obtained as pale yellow powder (yield: 23.5%).

Workup

  1. distillationAfter the solvent was distilled off
  2. additionwater was added
  3. extractionthe thus-formed mixture was extracted twice in a CHCl3 --MeOH (3:1)
  4. additionmixed solvent
  5. dry with materialThe extract was dried over MgSO4
  6. concentrationconcentrated under reduced pressure
  7. washSubsequent to elution
  8. customwith CHCl3, recrystallization

Sources & evidence

ORD record
ord-2568adea95614f71b5a6d9c05deacb37
Source dataset
uspto-grants-2000_01
Patent number
US06011033

Reaction notes

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