Water → Methyl 4-Hydroxyquinoline-2-carboxylate

HRID 2407759Notes

Reaction equation

[C:1]1([NH:7]/[C:8](=[CH:13]/[C:14]([O:16]C)=O)/[C:9]([O:11][CH3:12])=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.ClCCl.O>C1C=CC(C2C=CC=CC=2)=CC=1.C1C=CC(OC2C=CC=CC=2)=CC=1>[O:16]=[C:14]1[C:2]2[C:1](=[CH:6][CH:5]=[CH:4][CH:3]=2)[NH:7][C:8]([C:9]([O:11][CH3:12])=[O:10])=[CH:13]1

Participants

Conditions

Temperature: 250 °C

Procedure

A mixture of the compound prepared in Example 271 (0.980 g) in Dowtherm A (trade mark; 1 mL) was heated at 250° C. for 15 minutes. The mixture was cooled to room temperature and shaken between dichloromethane and water. The organic layer was dried, concentrated in vacuo and purified by column chromatography on silica gel (1-5% methanol in dichloromethane) to obtain the title compound (0.036 g) having the following physical data.

Workup

temperatureThe mixture was cooled to room temperature
customThe organic layer was dried
concentrationconcentrated in vacuo
custompurified by column chromatography on silica gel (1-5% methanol in dichloromethane)

Sources & evidence

ORD record: ord-cdde8fd665754f09b37229978437d7e6
Source dataset: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08809538B2

Reaction notes

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