Methyl iodide → 9-Acridinecarboxylic acid, methyl ester

HRID 509199Notes

Reaction equation

HRID 509199 reaction equation
[CH:1]1[C:14]2[C:5](=[N:6][C:7]3[C:12]([C:13]=2[C:15]([OH:17])=[O:16])=[CH:11][CH:10]=[CH:9][CH:8]=3)[CH:4]=[CH:3][CH:2]=1.CI.[C:20](=O)([O-])[O-].[K+].[K+]>CN(C=O)C.[Cl-].[Na+].O>[CH:11]1[C:12]2[C:7](=[N:6][C:5]3[C:14]([C:13]=2[C:15]([O:17][CH3:20])=[O:16])=[CH:1][CH:2]=[CH:3][CH:4]=3)[CH:8]=[CH:9][CH:10]=1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 94721Acridine-9-carboxylic acid

Product 1

HCID 212119-Acridinecarboxylic acid, methyl esterYield 78%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

A solution of acridine-9-carboxylic acid 81 (2.0 g, 8.96 mmol), methyl iodide (3.82 g, 26.9 mmol) and potassium carbonate (4.95 g, 35.8 mmol) in DMF (25 mL) was stirred at room temperature for 3 h then diluted with brine and extracted with EtOAc. The combined organic layers were dried over Na2SO4, filtered and concentrated to afford compound 82 (1.65 g, 78%) as a light yellow solid. LRMS (ESI): (calc) 237.25 (found) 238.2 (MH)+

Workup

  1. extractionextracted with EtOAc
  2. dry with materialThe combined organic layers were dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-db512d267e214cbba4c1bbd6b4ebb8a3
Source dataset
uspto-grants-2015_08
Patent number
US09096565B2

Reaction notes

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