Toluene → HCID 54012795, compound

HRID 1066350Notes

Reaction equation

HRID 1066350 reaction equation
[Na].[C:2]([O:10][CH2:11][CH3:12])(=[O:9])[CH2:3][C:4]([O:6][CH2:7][CH3:8])=[O:5].[Cl:13][C:14]1[CH:15]=[C:16]2[C:25](=[CH:26][CH:27]=1)[C:24](Cl)=[C:23]1[C:18]([CH:19]=[CH:20][C:21]([O:29][CH3:30])=[CH:22]1)=[N:17]2.C1(C)C=CC=CC=1>C(O)C.C(=O)([O-])[O-].[K+].[K+]>[Cl:13][C:14]1[CH:15]=[C:16]2[C:25](=[CH:26][CH:27]=1)[C:24]([CH:3]([C:4]([O:6][CH2:7][CH3:8])=[O:5])[C:2]([O:10][CH2:11][CH3:12])=[O:9])=[C:23]1[C:18]([CH:19]=[CH:20][C:21]([O:29][CH3:30])=[CH:22]1)=[N:17]2

Participants

7

Reactant 4

HCID 1140TolueneHCID 7761Diethyl MalonateHCID 665773,9-Dichloro-7-methoxyacridineHCID 5360545Sodium

Product 1

HCID 54012795HCID 54012795, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 11430Potassium CarbonateSolvent

Procedure

To a solution of sodium (1.3 g, 52 mmol) in ethanol (50 mL) was added diethyl malonate (8.8 g 55 mmol) followed by 6,9-dichloro-2-methoxyacridine (9.68 g, 35 mmol) and toluene (5 mL). The mixture was heated to reflux for 24 h, diluted with aqueous potassium carbonate, extracted with ethyl acetate, dried, and concentrated in vacuo to give solid which was purified by flash column chromatography (silica gel, 5-12% methanol:dichloromethane) to give the title compound. MS(ES) m/e 402.2 (M+H)+.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 24 h
  3. extractionextracted with ethyl acetate
  4. customdried
  5. concentrationconcentrated in vacuo
  6. customto give solid which
  7. customwas purified by flash column chromatography (silica gel, 5-12% methanol:dichloromethane)

Sources & evidence

ORD record
ord-51a868be027f484ead065b1f1afae61b
Source dataset
uspto-grants-2001_06
Patent number
US06242459B1

Reaction notes

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