Sulfuric acid magnesium salt (1:1) → 3-(4-Chlorophenyl)-2-isopropyl-7H-pyrano[2,3-e]indazol-4-one

HRID 14500Notes

Reaction equation

HRID 14500 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:17](=[O:18])[C:16]3[C:11](=[C:12]([CH:32]=O)[C:13](OS(C4C(C)=CC(C)=CC=4C)(=O)=O)=[CH:14][CH:15]=3)[O:10][C:9]=2[CH:34]([CH3:36])[CH3:35])=[CH:4][CH:3]=1.S([O-])([O-])(=O)=O.[Mg+2].C([O-])(=O)C.[NH4+:47].O.[NH2:49]N>C(O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:17](=[O:18])[C:16]3[C:11]([O:10][C:9]=2[CH:34]([CH3:36])[CH3:35])=[C:12]2[C:13](=[CH:14][CH:15]=3)[NH:49][N:47]=[CH:32]2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 24083Sulfuric acid magnesium salt (1:1)HCID 24654Hydrazine hydrate (1:1)HCID 517165Ammonium AcetateHCID 86625617HCID 86625617, compound

Product 1

HCID 687032613-(4-Chlorophenyl)-2-isopropyl-7H-pyrano[2,3-e]indazol-4-one

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
145 °C

Procedure

To a suspension of 2,4,6-trimethylbenzenesulfonic acid 3-(4-chlorophenyl)-8-formyl-2-isopropyl-4-oxo-4H-chromen-7-yl ester (391 mg, 0.745 mmol), magnesium sulphate (450 mg, 3.72 mmol) and ammonium acetate (230 mg, 2.98 mmol) in ethanol (15 ml) in a 20 ml microwave tube is added hydrazine hydrate (0.93 ml, 2.98 mmol). The tube is sealed and heated at 145° C. for ca. 80 min. The mixture is cooled to room temperature, and the volatiles are evaporated under reduced pressure. The residue is dissolved in dry pyridine (14 ml), the solution is transferred to a 20 ml microwave tube, the tube is sealed, and the mixture is heated at 190° C. for 100 min. The mixture is cooled and evaporated to dryness. The residue is purified by chromatography on silica gel using cyclohexane/ethyl acetate (6:1) as eluant.

Workup

  1. customThe tube is sealed
  2. temperatureThe mixture is cooled to room temperature
  3. customthe volatiles are evaporated under reduced pressure
  4. dissolutionThe residue is dissolved in dry pyridine (14 ml)
  5. customthe solution is transferred to a 20 ml microwave tube
  6. customthe tube is sealed
  7. temperaturethe mixture is heated at 190° C. for 100 min
  8. temperatureThe mixture is cooled
  9. customevaporated to dryness
  10. customThe residue is purified by chromatography on silica gel

Sources & evidence

ORD record
ord-1b847f9f58a34d30a91eb189bd764274
Source dataset
uspto-grants-2010_06
Patent number
US07732435B2

Reaction notes

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