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

HRID 2374144Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2374144
[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

Komponenten

6

Edukt 3

HCID 25517Ammonium ChlorideHCID 47383921,8-Naphthyridine-4-carbaldehydeHCID 178418573HCID 178418573, Verbindung

Produkt 1

HCID 445966671-[1,8]Naphthyridin-4-yl-ethanol

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1140TolueneLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

[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).

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-9c6974b6d9724137a4e5adc75f4700a2
Quelldatensatz
uspto-grants-2008_12
Patentnummer
US07462600B2

Notizen zur Reaktion

Wird geladen…