Sulfuric acid magnesium salt (1:1) → HCID 178434215, compound

HRID 14498Notes

Reaction equation

[C:1]([C:4]1[C:5](OS(C2C(C)=CC(C)=CC=2C)(=O)=O)=[CH:6][CH:7]=[C:8]2[C:13]=1[O:12][C:11]([CH:14]([CH3:16])[CH3:15])=[C:10]([C:17]1[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=1)[C:9]2=[O:24])(=O)[CH3:2].C([O-])(=O)C.[NH4+:42].S([O-])([O-])(=O)=O.[Mg+2].O.[NH2:50]N>C1(C)C=CC=CC=1.O.C(O)C>[Cl:23][C:20]1[CH:21]=[CH:22][C:17]([C:10]2[C:9](=[O:24])[C:8]3[C:13]([O:12][C:11]=2[CH:14]([CH3:15])[CH3:16])=[C:4]2[C:5](=[CH:6][CH:7]=3)[NH:50][N:42]=[C:1]2[CH3:2])=[CH:18][CH:19]=1

Participants

Conditions

Temperature: 140 °C

Procedure

2,4,6-Trimethylbenzenesulfonic acid 8-acetyl-3-(4-chlorophenyl)-2-isopropyl-4oxo-4H-chromen-7-yl ester (470 mg, 0.87 mmol), ammonium acetate (339 mg, 4.4 mmol) and magnesium sulfate (530 mg, 4.4 mmol) are dissolved/suspended in toluene (7 ml) and ethanol (7 ml) in a 20 ml capacity microwave tube. Hydrazine hydrate (0.136 ml, 4.4 mmol) is added, the tube is sealed, and the mixture is heated at 140° C. under microwave irradiation for 2 h. The reaction mixture is then poured into water (20 ml) and extracted with ethyl acetate (3×20 ml). The ethyl acetate extracts are combined, washed with saturated brine (50 ml), dried (MgSO4), filtered and evaporated to give a light brown solid. This is absorbed onto silica gel and purified by chromatography on silica gel using n-hexane/ethyl acetate (0-50% ethyl acetate) as eluant to give the product as a colourless solid.

Workup

customthe tube is sealed
extractionextracted with ethyl acetate (3×20 ml)
washwashed with saturated brine (50 ml)
dry with materialdried (MgSO4)
filtrationfiltered
customevaporated
customto give a light brown solid
customThis is absorbed onto silica gel
custompurified by chromatography on silica gel

Sources & evidence

ORD record: ord-608ddea0563b41de8961ecbe41bd6963
Source dataset: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07732435B2

Reaction notes

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