Sodium Hydroxide → 5-[5-(2,2'-Dimethylbiphenyl-4-yl)-1,2,4-oxadiazol-3-yl]-2-hydroxybenzoic acid

HRID 219926Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 219926
[CH3:1][C:2]1[CH:7]=[C:6]([C:8]2[O:12][N:11]=[C:10]([C:13]3[CH:14]=[CH:15][C:16]([OH:23])=[C:17]([CH:22]=3)[C:18]([O:20]C)=[O:19])[N:9]=2)[CH:5]=[CH:4][C:3]=1[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[CH3:30].[OH-].[Na+]>>[CH3:1][C:2]1[CH:7]=[C:6]([C:8]2[O:12][N:11]=[C:10]([C:13]3[CH:14]=[CH:15][C:16]([OH:23])=[C:17]([CH:22]=3)[C:18]([OH:20])=[O:19])[N:9]=2)[CH:5]=[CH:4][C:3]=1[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[CH3:30]

Komponenten

3

Edukt 2

HCID 14798Sodium HydroxideHCID 136346390Methyl 5-[5-(2,2'-dimethylbiphenyl-4-yl)-1,2,4-oxadiazol-3-yl]-2-hydroxybenzoate

Produkt 1

HCID 1358693955-[5-(2,2'-Dimethylbiphenyl-4-yl)-1,2,4-oxadiazol-3-yl]-2-hydroxybenzoic acidAusbeute 90 %

Versuchsvorschrift

The title compound was prepared following procedure described for example 4, step 2, but starting from methyl 5-[5-(2,2′-dimethylbiphenyl-4-yl)-1,2,4-oxadiazol-3-yl]-2-hydroxybenzoate, obtained in step 1, and using 25 eq. of NaOH at 60° C. for 6 h. Solvents were concentrated and DCM (20 mL) was added. It was washed with HCl 1M. The organic layer was then dried over magnesium sulfate, filtered and concentrated to afford the title compound as a pale orange solid (18 mg; 90%). 1H NMR (DMSO-d6, 300 MHz) δ 8.54 (d, J=2.1 Hz, 1H), 8.22-8.17 (m, 2H), 8.08-8.05 (m, 1H), 7.38-7.28 (m, 4H), 7.19-7.12 (m, 2H), 2.14 (s, 3H), 2.04 (s, 3H). LC/MS (Method A): 385.0 (M−H)−. HPLC (Method A) Rt 5.49 min (Purity: 97.2%).

Aufarbeitung

  1. customThe title compound was prepared following procedure
  2. customobtained in step 1
  3. customat 60° C.
  4. customfor 6 h
  5. concentrationSolvents were concentrated
  6. additionDCM (20 mL) was added
  7. washIt was washed with HCl 1M
  8. dry with materialThe organic layer was then dried over magnesium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-fe62a9843f1e4905bca6259030284435
Quelldatensatz
uspto-grants-2012_06
Patentnummer
US08202865B2

Notizen zur Reaktion

Wird geladen…