Hydrochloric Acid → N-(4-bromo-2-fluoro-benzyl)-2-hydroxy-4-methoxy-benzamide

HRID 457943

Reaktionsgleichung

Reaktionsgleichung von HRID 457943
[Br:1][C:2]1[CH:22]=[CH:21][C:5]([CH2:6][N:7]2[C:12](=[O:13])[C:11]3[CH:14]=[CH:15][C:16]([O:18][CH3:19])=[CH:17][C:10]=3[O:9]C2=O)=[C:4]([F:23])[CH:3]=1.[OH-].[K+].Cl>C(O)C>[Br:1][C:2]1[CH:22]=[CH:21][C:5]([CH2:6][NH:7][C:12](=[O:13])[C:11]2[CH:14]=[CH:15][C:16]([O:18][CH3:19])=[CH:17][C:10]=2[OH:9])=[C:4]([F:23])[CH:3]=1

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 184681743-(4-Bromo-2-fluoro-benzyl)-7-methoxy benzo[e][1,3]oxazine-2,4-dione

Produkt 1

HCID 18468133N-(4-bromo-2-fluoro-benzyl)-2-hydroxy-4-methoxy-benzamideAusbeute 71 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A solution of 3-(4-bromo-2-fluoro-benzyl)-7-methoxy benzo[e] [1,3] oxazine-2,4-dione (1.67 g, 4.4 mmol) in ethanol (80 mL, 0.06 M) was cooled to 0° C. and treated with aq KOH (0.673 g, 11.9 mmol, 1.2 M). After 3 h, the reaction was acidified to pH 1–2 with 2 N HCl and extracted with ethyl acetate (3×). The combined organic extracts were washed with saturated aq NaCl, dried over Na2SO4, filtered and concentrated. The crude solid was recrystallized from heptane and ethyl acetate to give N-(4-bromo-2-fluoro-benzyl)-2-hydroxy-4-methoxy-benzamide as a white crystalline solid (1.10 g, 71%): mp 128–129.5° C.; Rf 0.28 (25% ethyl acetate in heptane); 1H NMR (DMSO-d6, 300 MHz) δ 12.70 (br s, 1 H), 9.14 (br t, J=5.2 Hz, 1 H), 7.80 (d, J=8.5 Hz, 1 H), 7.50 (d, J=8.5 Hz, 1 H), 7.40–7.25 (m, 2 H), 6.50–6.48 (m, 2 H), 4.45 (d, J=5.2 Hz, 2 H), 3.75 (s, 3 H). ESI-LC/MS m/z calcd for C15H13BrFNO2: 353.0; found 352.0 (M−1)−. Anal. calcd for C15H13BrFNO2: C, 50.87; H, 3.70; N, 3.95. Found C, 50.70; H, 3.73; N, 3.91.

Aufarbeitung

  1. extractionextracted with ethyl acetate (3×)
  2. washThe combined organic extracts were washed with saturated aq NaCl
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude solid was recrystallized from heptane and ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-9b01dda2d9ee4925828ed3a24f096f09
Quelldatensatz
uspto-grants-2007_03
Patentnummer
US07189749B2

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