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

HRID 2229532

Reaktionsgleichung

Reaktionsgleichung von HRID 2229532
[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

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, 1H), 9.14 (br t, J=5.2 Hz, 1H), 7.80 (d; J=8.5 Hz, 1H), 7.50 (d, J=8.5 Hz, 1H), 7.40-7.25 (m, 2H), 6.50-6.48 (m, 2H), 4.45 (d, J=5.2 Hz, 2H), 3.75 (s, 3H). 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-e9d8ab47e94141b2951c640e1c8b242b
Quelldatensatz
uspto-grants-2002_07
Patentnummer
US06420426B1

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