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

HRID 1993394Notes

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-hydroxy-phenyl)-5-oxo-pyrrolidine-3-carboxylic acid methyl ester (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 reaction 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 colorless glass. MS (ESI pos. ion) m/z: 423.2 (M+H). Calc'd Exact Mass for C23H22N2O6: 422.43.

Workup

temperatureThe reaction 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)
customto provide colorless glass

Sources & evidence

ORD record: ord-91c75213dccb481ca5b4cbd5119b4f66
Source dataset: uspto-grants-2010_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07652009B2

Reaction notes

Loading…