Sodium borohydride → 7-(Methoxymethoxy)-8-nitroquinolin-2-yl methanol

HRID 1920673Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1920673
[BH4-].[Na+].[CH3:3][O:4][CH2:5][O:6][C:7]1[C:16]([N+:17]([O-:19])=[O:18])=[C:15]2[C:10]([CH:11]=[CH:12][C:13]([CH:20]=[O:21])=[N:14]2)=[CH:9][CH:8]=1>CCO.C(Cl)(Cl)Cl>[CH3:3][O:4][CH2:5][O:6][C:7]1[C:16]([N+:17]([O-:19])=[O:18])=[C:15]2[C:10]([CH:11]=[CH:12][C:13]([CH2:20][OH:21])=[N:14]2)=[CH:9][CH:8]=1

Komponenten

5

Edukt 2

HCID 4311764Sodium borohydrideHCID 25228376HCID 25228376, Verbindung

Produkt 1

HCID 252283787-(Methoxymethoxy)-8-nitroquinolin-2-yl methanolAusbeute 46,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 6212ChloroformLösungsmittel

Versuchsvorschrift

Referring to FIG. 20, NaBH4 was added to a solution of 9a (18.1 mg, 0.0691 mmol) in absolute EtOH (5 mL). The reaction mixture was stirred for 15 min, diluted with chloroform, washed with water followed by brine. The organic layer was dried over Na2SO4 and the solvent was evaporated to afford 10a (8.3 mg, 0.032 mmol, 45%) as a yellow solid: 1H NMR (CDCl3) δ 8.14 (1H, d, J=8.8 Hz), 7.90 (1H, d, J=9.2 Hz), 7.58 (1H, d, J=9.2 Hz), 7.31 (1H, d, J=8.4 Hz), 5.39 (2H, s), 4.91 (2H, s), 3.54 (3H, s); 13C NMR (CDCl3) δ 162.4, 149.0, 139.1, 136.7, 131.9, 130.6, 123.1, 118.5, 116.3, 95.4, 64.5, 57.1; FTIR (neat) 3583, 2923, 1635, 1516, 1263, 1157, 1084, 1047, 931, 916, 804 cm−1; MS (ESI) m/z calculated for (C12H12N2O5+H)+ 265, found 265; HRMS (ESI) m/z calculated for (C12H12N2O5+H)+ 265.0824, found 265.0814.

Aufarbeitung

  1. washwashed with water
  2. dry with materialThe organic layer was dried over Na2SO4
  3. customthe solvent was evaporated

Quellen und Nachweise

ORD-Eintrag
ord-b76f742148f44fabbc5dc630079fb921
Quelldatensatz
uspto-grants-2012_05
Patentnummer
US08173620B2

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