Water → HCID 22742432, compound

HRID 48186Notes

Reaction equation

HRID 48186 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]2[C:6](=O)[C:7]3[C:12]([N:13]([CH2:17][CH2:18][CH2:19][Br:20])[C:14]=2[C:15]=1[CH3:16])=[CH:11][CH:10]=[CH:9][CH:8]=3.[CH3:22][Li].O>O1CCCC1.C(OCC)C>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]2[C:6](=[CH2:22])[C:7]3[C:12]([N:13]([CH2:17][CH2:18][CH2:19][Br:20])[C:14]=2[C:15]=1[CH3:16])=[CH:11][CH:10]=[CH:9][CH:8]=3

Participants

6

Reactant 3

HCID 962WaterHCID 22742431HCID 22742431, compoundHCID 178418348HCID 178418348, compound

Product 1

HCID 22742432HCID 22742432, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

0.1 g of 3,4-dimethyl-10-(3-bromopropyl)-9-acridone was dissolved in 5 ml of dry tetrahydrofuran. Then 0.36 ml of methyllithium (a 1.4 M solution in diethyl ether) was added dropwise at −78° C. After stirring at the same temperature for 1 hr, water was added to the liquid reaction mixture followed by extraction with ethyl acetate. The organic layer was washed with water and dried over anhydrous magnesium sulfate. After evaporating the solvent under reduced pressure, the residue was purified by silica gel column chromatography to give 0.1 g of the title compound.

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe organic layer was washed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customAfter evaporating the solvent under reduced pressure
  5. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-80b28bb1307f43a6bfbe11602a536fee
Source dataset
uspto-grants-2004_03
Patent number
US06703388B2

Reaction notes

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