Sulfuric Acid → HCID 58424967, compound

HRID 2409401Notes

Reaction equation

HRID 2409401 reaction equation
[CH3:1][O:2][C:3]1[CH:26]=[CH:25][C:6]2[N:7](CC3C=CC(OC)=CC=3)[C:8](=[O:15])[C:9]3[CH:10]=[CH:11][CH:12]=[N:13][C:14]=3[C:5]=2[CH:4]=1.C1(OC)C=CC=CC=1.S(=O)(=O)(O)O.C(=O)(O)[O-].[Na+]>FC(F)(F)C(O)=O>[CH3:1][O:2][C:3]1[CH:26]=[CH:25][C:6]2[NH:7][C:8](=[O:15])[C:9]3[CH:10]=[CH:11][CH:12]=[N:13][C:14]=3[C:5]=2[CH:4]=1

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 7519AnisoleHCID 516892Sodium BicarbonateHCID 58424923HCID 58424923, compound

Product 1

HCID 58424967HCID 58424967, compoundYield 78.9%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Conditions

Temperature
90 °C

Procedure

9-Methoxy-6-(4-methoxybenzyl)benzo[h][1,6]naphthyridine-5(6H)-one (50 mg, 0.14 mmol) prepared in step 3 of Example 3 was dissolved in trifluoroacetic acid (5 ml), sequentially added with anisol (157 μl, 1.44 mmol) and 12N sulfuric acid (240 μl, 2.89 mmol. The mixture was stirred for one day at 90° C. The reaction mixture was cooled to room temperature and poured into a cold saturated sodium bicarbonate aqueous solution. After extraction with chloroform, the organic layer was washed with brine and dried over anhydrous sodium sulfate. After evaporation of the solvent, the residue was washed with ethyl acetate, filtered, and dried in vacuo to obtain the title compound (25 mg, yield: 77%, white solid).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. extractionAfter extraction with chloroform
  3. washthe organic layer was washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customAfter evaporation of the solvent
  6. washthe residue was washed with ethyl acetate
  7. filtrationfiltered
  8. customdried in vacuo

Sources & evidence

ORD record
ord-ac37ea75dab64cbd93a512e44c33ba9a
Source dataset
uspto-grants-2014_08
Patent number
US08815891B2

Reaction notes

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