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Ammonium Chloride → (6-Bromo-naphthalen-2-yl)-(6,7-dimethoxy-quinolin-4-yl)-methanol

HRID 1925262
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1925262
C1(S([C:9]2[C:18]3[C:13](=[CH:14][C:15]([O:21][CH3:22])=[C:16]([O:19][CH3:20])[CH:17]=3)[N:12]=[CH:11][CH:10]=2)=O)C=CC=CC=1.C1([Mg]Br)C=CC=CC=1.[Br:31][C:32]1[CH:33]=[C:34]2[C:39](=[CH:40][CH:41]=1)[CH:38]=[C:37]([CH:42]=[O:43])[CH:36]=[CH:35]2.[NH4+].[Cl-]>C1COCC1>[Br:31][C:32]1[CH:33]=[C:34]2[C:39](=[CH:40][CH:41]=1)[CH:38]=[C:37]([CH:42]([C:9]1[C:18]3[C:13](=[CH:14][C:15]([O:21][CH3:22])=[C:16]([O:19][CH3:20])[CH:17]=3)[N:12]=[CH:11][CH:10]=1)[OH:43])[CH:36]=[CH:35]2
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Komponenten

6

Edukt 4

HCID 25517Ammonium ChlorideHCID 134770296-Bromonaphthalene-2-carbaldehydeHCID 675205384-Benzenesulfinyl-6,7-dimethoxy-quinolineHCID 178418255HCID 178418255, Verbindung

Produkt 1

HCID 67520432(6-Bromo-naphthalen-2-yl)-(6,7-dimethoxy-quinolin-4-yl)-methanol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028
Tetrahydrofuran
Lösungsmittel
2×

Versuchsvorschrift

To a solution of 4-benzenesulfinyl-6,7-dimethoxy-quinoline (step b, 1 g, 3.2 mmol) in THF (15 mL) at −10° C., was added phenylmagnesium bromide (1M in THF, 3.5 mL, 3.5 mmol). The reaction was warmed to RT and stirred for 20 min. 6-Bromo-naphthalene-2-carbaldehyde (Step d, 0.75 g, 3.2 mmol) was added in THF. The resulting mixture was stirred at RT for 2 h, then poured into saturated NH4Cl solution and extracted with ethyl acetate 3×. The combined organic layer was washed with brine, dried over Na2SO4, filtered and concentrated in vacuo. The crude was purified by silica gel column chromatography (15-35% acetone/CH2Cl2) to give the titled compound. MS (ESI, pos. ion) m/z: 424.1 (M+1).

Aufarbeitung

  1. stirringThe resulting mixture was stirred at RT for 2 h
  2. extractionextracted with ethyl acetate 3×
  3. washThe combined organic layer was washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude was purified by silica gel column chromatography (15-35% acetone/CH2Cl2)

Quellen und Nachweise

ORD-Eintrag
ord-a5033e7ff9c64061bdf316ac80790074
Quelldatensatz
uspto-grants-2012_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08178557B2

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