Water → 4-Hydroxymethyl-6-methoxyquinoline

HRID 1169662Notes

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 1 M 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-e7a3f99d0c5d4ad08edb45343b429742
Source dataset: uspto-grants-2010_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07825115B2

Reaction notes

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