Glycerol → 7-Isopropyl-6-methoxyquinoline

HRID 502631Notes

Reaction equation

[CH:1]([C:4]1[CH:5]=[C:6]([CH:8]=[CH:9][C:10]=1[O:11][CH3:12])[NH2:7])([CH3:3])[CH3:2].O[CH2:14][CH:15]([CH2:17]O)O.OS(O)(=O)=O.C([O-])(O)=O.[Na+]>O.C(OCC)(=O)C>[CH:1]([C:4]1[CH:5]=[C:6]2[C:8]([CH:14]=[CH:15][CH:17]=[N:7]2)=[CH:9][C:10]=1[O:11][CH3:12])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 3-isopropyl-4-methoxyaniline (4.22 g, 23.6 mmol), 5.87 g (63.7 mmole) of glycerol and 3.25 g (14 mmol) of As2O5 was heated to 100° C. with stirring At 100° C., 4.0 mL of concentrated H2SO4 was added dropwise. The mixture was heated at 150-160° C. for six hours, then cooled to 80° C., and 20 mL water was added, followed by aqueous saturated NaHCO3 until the mixture reached pH7-8. The mixture was diluted with 100 mL of water and 300 mL of ethyl acetate and the solution mixture was decanted from insolubles. The organic layer was separated, washed with brine, dried (MgSO4), filtered and concentrated under reduced pressure. The resulting residue was purified by column chromatography with silica eluting with 20% ethyl acetate in hexanes to give 2.58 g of 7-isopropyl-6-methoxyquinoline, together with 0.65 g of 6-hydroxy-7-isopropylquinoline as a minority product.

Workup

temperatureThe mixture was heated at 150-160° C. for six hours
temperaturecooled to 80° C.
customthe solution mixture was decanted from insolubles
customThe organic layer was separated
washwashed with brine
dry with materialdried (MgSO4)
filtrationfiltered
concentrationconcentrated under reduced pressure
customThe resulting residue was purified by column chromatography with silica eluting with 20% ethyl acetate in hexanes

Sources & evidence

ORD record: ord-c8c87a61e6ba4ad98e80a85693fbbff5
Source dataset: uspto-grants-2010_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07776872B2

Reaction notes

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