4-Chloro-6,7-dimethoxyquinoline → HCID 68420806, compound

HRID 1993371Notes

Reaction equation

Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:14][CH3:15])=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[CH:4][CH:3]=1.[CH3:16][O:17][C:18]([CH:20]1[CH2:24][C:23](=[O:25])[N:22]([C:26]2[CH:31]=[CH:30][C:29]([OH:32])=[CH:28][CH:27]=2)[CH2:21]1)=[O:19]>CN(C1C=CN=CC=1)C.C1(C)C=CC=CC=1.CCOC(C)=O>[CH3:13][O:12][C:9]1[CH:10]=[C:11]2[C:6](=[CH:7][C:8]=1[O:14][CH3:15])[N:5]=[CH:4][CH:3]=[C:2]2[O:32][C:29]1[CH:28]=[CH:27][C:26]([N:22]2[C:23](=[O:25])[CH2:24][CH:20]([C:18]([O:17][CH3:16])=[O:19])[CH2:21]2)=[CH:31][CH:30]=1

Participants

Conditions

Temperature: 180 °C

Procedure

A mixture of 4-chloro-6,7-dimethoxy-quinoline (1.0 g, 4.45 mmol), 1-(4-hydroxyphenyl)-5-oxo-pyrrolidine-3-carboxylic acid methyl ester (Step 1, 1.6 g, 6.7 mmol) and DMAP (0.55 g, 4.45 mmol) in 30 mL of toluene (in 5 microwave tubes) was heated in a microwave (Personal Chemistry, Emrys Optimizer) at 180° C. for 1 h. The mixture was cooled to RT and diluted with 60 mL of EtOAc. The solution was washed with 20 mL of satd. NaHCO3 followed by 20 mL of brine, dried over Na2SO4 and concentrated in vacuo. The residue was further purified with silica gel column chromatography (100% EtOAc to 15% MeOH in EtOAc) to provide the title compound as colorless glass. MS (ESI pos. ion) m/z: 423.2 (M+H). Calc'd Exact Mass for C23H22N2O6: 422.43.

Workup

temperatureThe mixture was cooled to RT
washThe solution was washed with 20 mL of satd
dry with materialdried over Na2SO4
concentrationconcentrated in vacuo
customThe residue was further purified with silica gel column chromatography (100% EtOAc to 15% MeOH in EtOAc)

Sources & evidence

ORD record: ord-493bbd3054964df0b56d42d785a2c636
Source dataset: uspto-grants-2010_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07652009B2

Reaction notes

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