Water → 4-Hydroxymethyl-6-methoxyquinoline

HRID 899967Notes

Reaction equation

[H-].[H-].[H-].[H-].[Li+].[Al+3].C([O:9][C:10]([C:12]1[C:21]2[C:16](=[CH:17][CH:18]=[C:19]([O:22][CH3:23])[CH:20]=2)[N:15]=[CH:14][CH:13]=1)=O)C.O.C(OCC)(=O)C>C1COCC1>[OH:9][CH2:10][C:12]1[C:21]2[C:16](=[CH:17][CH:18]=[C:19]([O:22][CH3:23])[CH:20]=2)[N:15]=[CH:14][CH:13]=1

Participants

Conditions

Temperature: 20 °C

Procedure

17 ml of a 1M solution of LiAlH4 in THF are added dropwise to a solution of 4 g of 4-ethoxycarbonyl-6-methoxyquinoline in 100 ml of anhydrous THF, under an inert atmosphere of argon at a temperature in the region of 5° C. The reaction medium is maintained with stirring for 16 hours at a temperature in the region of 20° C. 50 ml of water and 50 ml of ethyl acetate are added. After separation of the phases by settling, the organic phase is dried over sodium sulfate, filtered and then concentrated under reduced pressure. The foam obtained is purified by flash chromatography (SiO2, EtOAc as eluent, Ar). The fractions containing the product are concentrated under reduced pressure. 0.86 g of 4-hydroxymethyl-6-methoxyquinoline is thus obtained, the characteristics of which product are as follows:

Workup

temperatureThe reaction medium is maintained
customAfter separation of the phases
dry with materialthe organic phase is dried over sodium sulfate
filtrationfiltered
concentrationconcentrated under reduced pressure
customThe foam obtained
customis purified by flash chromatography (SiO2, EtOAc as eluent, Ar)
additionThe fractions containing the product
concentrationare concentrated under reduced pressure

Sources & evidence

ORD record: ord-647272b0cf1d4b0a9fd9d4a82171054f
Source dataset: uspto-grants-2008_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07354933B2

Reaction notes

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