Glycerol → 8-Methyl-7-nitroquinoline

HRID 1936585Notes

Reaction equation

[CH3:1][C:2]1[C:8]([N+:9]([O-:11])=[O:10])=[CH:7][CH:6]=[CH:5][C:3]=1[NH2:4].O.[As+3]=O.S(=O)(=O)(O)O.[OH-].[NH4+].O[CH2:23][CH:24]([CH2:26]O)O>O.C(OCC)(=O)C>[CH3:1][C:2]1[C:8]([N+:9]([O-:11])=[O:10])=[CH:7][CH:6]=[C:5]2[C:3]=1[N:4]=[CH:26][CH:24]=[CH:23]2

Participants

Conditions

Temperature: 150 °C

Procedure

To a suspension of 2 g of 2-methyl-3-nitroaniline and 1.02 g of arsenic(v) oxide hydrate are added 2.88 mL of glycerin followed by 1.09 mL of concentrated sulfuric acid. The resulting black slurry is stirred at about 150° C. for 4 hours. The black oil is cooled to room temperature, diluted with water and poured into a mixture of 25% aqueous ammonium hydroxide and ethyl acetate. The organic layer is washed with water followed by brine. The aqueous layers are extracted with ethyl acetate; the combined organic layers are dried over magnesium sulfate, filtered and rotary evaporated. The residue is purified by flash column chromatography on silica gel, eluting with 50% ethyl acetate/hexanes followed by recrystallization from hexanes/methylene chloride to provide 1.45 g of 8-methyl-7-nitroquinoline as a pale brown solid.

Workup

temperatureThe black oil is cooled to room temperature
washThe organic layer is washed with water
extractionThe aqueous layers are extracted with ethyl acetate
dry with materialthe combined organic layers are dried over magnesium sulfate
filtrationfiltered
customThe residue is purified by flash column chromatography on silica gel
washeluting with 50% ethyl acetate/hexanes
customfollowed by recrystallization from hexanes/methylene chloride

Sources & evidence

ORD record: ord-86882a9f12fe4fe5a52672b630844f74
Source dataset: uspto-grants-2002_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06391878B2

Reaction notes

Loading…