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

HRID 219926Notes

Reaction equation

HRID 219926 reaction equation
[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]

Participants

3

Reactant 2

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

Product 1

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

Procedure

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%).

Workup

  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

Sources & evidence

ORD record
ord-fe62a9843f1e4905bca6259030284435
Source dataset
uspto-grants-2012_06
Patent number
US08202865B2

Reaction notes

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