Aluminium lithium hydride → 2-[[(6-methoxy-2-pyridinyl)amino]methyl]-6-methylPhenol

HRID 2170005Notes

Reaction equation

[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH:7][C:8]1[C:24]([CH3:25])=[CH:23][CH:22]=[CH:21][C:9]=1[C:10]([NH:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([O:19][CH3:20])[N:14]=1)=O>O1CCOCC1.C(OCC)(=O)C>[CH3:20][O:19][C:15]1[N:14]=[C:13]([NH:12][CH2:10][C:9]2[CH:21]=[CH:22][CH:23]=[C:24]([CH3:25])[C:8]=2[OH:7])[CH:18]=[CH:17][CH:16]=1

Participants

Conditions

Temperature: 80 °C

Procedure

80 mg (2.1 mmol, 6 eq) of lithium aluminium hydride are added in small fractions to a mixture of 90 mg (0.35 mmol) of 2-hydroxy-N-(6-methoxypyridin-2-yl)-3-methylbenzamide in 10 ml of dioxane. The reaction medium is heated at 80° C. for 16 h. 80 mg (2.1 mmol, 6 eq) of lithium aluminium hydride are added again and the medium is heated at 80° C. for 4 h. The reaction medium is diluted with 50 ml of ethyl acetate and washed with 50 ml of a saturated solution of ammonium chloride, and then twice with 50 ml of water. The organic phase is dried over magnesium sulphate, filtered and concentrated to dryness. The residue is purified by chromatography over silica, eluting with a heptane/ethyl acetate (1/1) mixture. 2-[(6-methoxypyridin-2-ylamino)methyl]-6-methylphenol is obtained in the form of a white solid.

Workup

temperaturethe medium is heated at 80° C. for 4 h
washwashed with 50 ml of a saturated solution of ammonium chloride
dry with materialThe organic phase is dried over magnesium sulphate
filtrationfiltered
concentrationconcentrated to dryness
customThe residue is purified by chromatography over silica
washeluting with a heptane/ethyl acetate (1/1) mixture

Sources & evidence

ORD record: ord-a84bb94c49174eaab20a011f6c1e30b2
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09050266B2

Reaction notes

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