Dichloromethane → HCID 12045061, compound

HRID 1829707Notes

Reaction equation

[OH:1][C:2]1[C:3]([C:13]([OH:15])=[O:14])=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:9]([CH3:12])[CH:8]=[CH:7]2.[OH-].[K+].ClCCl>C(O)CCC>[OH:1][C:2]1[C:3]([C:13]([O:15][CH2:3][CH2:2][CH2:11][CH3:6])=[O:14])=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:9]([CH3:12])[CH:8]=[CH:7]2

Participants

Conditions

Temperature: 20 °C

Procedure

A mixture of 8-hydroxy-7-quinaldinecarboxylic acid 1 (12 g, 59 mmol) and polyphosphoric acid (30 g) in 60 ml of n-butanol is heated at 100° C. for 72 hours during which additional portions of 30 g of polyphosphoric acid and 30 ml of n-butanol are regularly added every 12 hours. After cooling to 20° C., the reaction mixture is brought to pH 4 with a 6 N potassium hydroxide solution, and then 200 ml of dichloromethane are added. The phases are separated, and the aqueous phase extracted with dichloromethane. The combined organic phases are dried over magnesium sulfate and concentrated under reduced pressure. The residue is chromatographed on a silica column, eluting with a 1/1 cyclohexane/ethyl acetate mixture so as to give 11 g (72%) of n-butyl 8-hydroxy-2-methylquinoline-7-carboxylate in the form of a white solid.

Workup

additionare regularly added every 12 hours
customThe phases are separated
extractionthe aqueous phase extracted with dichloromethane
dry with materialThe combined organic phases are dried over magnesium sulfate
concentrationconcentrated under reduced pressure
customThe residue is chromatographed on a silica column
washeluting with a 1/1 cyclohexane/ethyl acetate mixture so as

Sources & evidence

ORD record: ord-274f4c82f75d49a181fe2637e547972f
Source dataset: uspto-grants-2006_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07064133B2

Reaction notes

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