Sulfuric Acid → HCID 69157054, compound

HRID 750251Notes

Reaction equation

HRID 750251 reaction equation
[CH3:1][O:2][C:3]([C:5]1O[C:7](=[O:23])[C:8]2[C:13]([C:14]=1[C:15]1[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][CH:16]=1)=[CH:12][C:11]([Cl:22])=[CH:10][CH:9]=2)=[O:4].COC(C1OC(=O)C2C(C=1C1C=CC(C)=CC=1)=CC=C(Cl)C=2)=O.[CH2:47]([NH:50][NH2:51])[CH2:48][OH:49].S(=O)(=O)(O)O>CO>[CH3:1][O:2][C:3]([C:5]1[N:51]([NH:50][CH2:47][CH2:48][OH:49])[C:7](=[O:23])[C:8]2[C:13]([C:14]=1[C:15]1[CH:16]=[CH:17][C:18]([CH3:21])=[CH:19][CH:20]=1)=[CH:12][C:11]([Cl:22])=[CH:10][CH:9]=2)=[O:4]

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 80172-HydrazinoethanolHCID 69156376HCID 69156376, compoundHCID 69156599HCID 69156599, compound

Product 1

HCID 69157054HCID 69157054, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution (5.0 ml) of 6-chloro-1-oxo-4-(p-tolyl)-1H-isochromen-3-carboxylic acid methyl ester and 7-chloro-1-oxo-4-p-tolyl-1H-isochromen-3-carboxylic acid methyl ester (mixture, 250 mg) in methanol was added hydrazine ethanol (540 μl), and the mixture was heated under reflux for 2 hrs. After cooling the reaction mixture, conc. sulfuric acid (0.5 ml) was added to the reaction mixture, and the mixture was stirred at room temperature for 18 hrs. The solvent was removed under reduced pressure and the residue was partitioned between water and ethyl acetate. The organic layer was dried over magnesium sulfate and concentrated under reduced pressure. The residue was purified by medium pressure preparative LC (hexane/ethyl acetate=5/1-2/3) to give the title compound (50 mg) as colorless crystals.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 2 hrs
  3. additionwas added to the reaction mixture
  4. customThe solvent was removed under reduced pressure
  5. customthe residue was partitioned between water and ethyl acetate
  6. dry with materialThe organic layer was dried over magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by medium pressure preparative LC (hexane/ethyl acetate=5/1-2/3)

Sources & evidence

ORD record
ord-b8858376a7dc4f49b5841d709511452f
Source dataset
uspto-grants-2008_07
Patent number
US07402595B2

Reaction notes

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