Ammonium Chloride → 1-[1,8]Naphthyridin-4-yl-ethanol

HRID 2374144Notes

Reaction equation

[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][N:9]=2)[C:4]([CH:11]=[O:12])=[CH:3][CH:2]=1.[CH3:13][Mg]Br.[Cl-].[NH4+]>C1(C)C=CC=CC=1.C1COCC1>[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][N:9]=2)[C:4]([CH:11]([OH:12])[CH3:13])=[CH:3][CH:2]=1

Participants

Conditions

Temperature: 0 °C

Procedure

[1,8]Naphthyridine-4-carbaldehyde (0.300 g, 1.90 mmol) was dissolved in a mixture of anhydrous toluene (10 mL) and anhydrous THF (10 mL). The solution was cooled to 0° C. and methyl magnesium bromide (1.62 mL of 1.4M in THF/toluene) was added slowly and the solution stirred 1 h while allowing to warm to RT. Satd. aq. ammonium chloride was added until the solution reached a bright yellow color and precipitate was apparent. The solution was passed through a syringe filter and into water, where it was extracted with EtOAc (3×30 mL). The combined organic fractions were dried over Na2SO4, filtered, and concentrated under vacuum. The product was purified (SGC using MeCN:hexanes eluant in 1:1 ratio initially, then switching to DCM:MeOH:NH4OH eluant in 89:10:1 ratio to finish the compound elution) yielding the title compound (0.079 g). MS (ESI+) for m/z 175 (M+H)+. 1H NMR (CDCl3) δ 8.73 (m, 1H), 8.64 (d, 1H), 8.38 (m, 1H), 7.52 (d, 1H), 7.25 (dd, 1H), 6.32 (bs, 1H), 5.58 (dd, 1H), 1.48 (s, 3H).

Workup

temperatureto warm to RT
customThe solution was passed through a syringe
filtrationfilter and into water, where it
extractionwas extracted with EtOAc (3×30 mL)
dry with materialThe combined organic fractions were dried over Na2SO4
filtrationfiltered
concentrationconcentrated under vacuum
customThe product was purified (SGC
washthe compound elution)

Sources & evidence

ORD record: ord-9c6974b6d9724137a4e5adc75f4700a2
Source dataset: uspto-grants-2008_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07462600B2

Reaction notes

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