Sodium Hydroxide → HCID 9880243, compound

HRID 431955Notes

Reaction equation

HRID 431955 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[N:11]=[C:10]([C:12]2[CH:17]=[C:16]([C:18]([O:20]C)=[O:19])[CH:15]=[C:14]([O:22][CH2:23][CH:24]=[CH2:25])[CH:13]=2)[O:9][N:8]=1.[OH-].[Na+]>CO>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[N:11]=[C:10]([C:12]2[CH:17]=[C:16]([C:18]([OH:20])=[O:19])[CH:15]=[C:14]([O:22][CH2:23][CH:24]=[CH2:25])[CH:13]=2)[O:9][N:8]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 9902359HCID 9902359, compound

Product 1

HCID 9880243HCID 9880243, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A stirred suspension of 3-(2-Pyridyl)-5-(3-allyloxy-5-(methoxycarbonyl)phenyl)-1,2,4-oxadiazole (1.8 g, 5.28 mmol) in methanol (40 mL) was treated with 1M sodium hydroxide (7.9 mL, 7.9 mmol) and the reaction stirred at ambient temperature for 36 hours. The solvent was removed in vacuo, and the residue was dissolved in water (30 mL) and then acidified (pH 4-5) by the addition of 2N hydrogen chloride. The resulting precipitate was collected and dried to afford 1.6 (94%) of 3-(2-pyridyl)-5-(3-allyloxy-5-carboxyphenyl)-1,2,4-oxadiazole: 1H NMR (DMSO): δ-8.81 (d, 1H), 8.29 (s, 1H), 8.22 (d, 1H), 8.05 (m, 1H), 7.91 (s, 1H), 7.76 (s, 1H), 7.65 (m, 1H), 6.09 (m, 1H), 5.47 (dd, 1H), 5.33 (dd, 1H), 4.80 (d, 2H).

Workup

  1. customThe solvent was removed in vacuo
  2. dissolutionthe residue was dissolved in water (30 mL)
  3. additionby the addition of 2N hydrogen chloride
  4. customThe resulting precipitate was collected
  5. customdried

Sources & evidence

ORD record
ord-2528751ffc504478ade0d8b0ad68174e
Source dataset
uspto-grants-2003_12
Patent number
US06660753B2

Reaction notes

Loading…