Sodium Hydroxide → HCID 9814721, compound

HRID 431954Notes

Reaction equation

HRID 431954 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]([O:18][CH3:19])[CH:15]=[C:14]([C:20]([O:22]C)=[O:21])[CH:13]=2)[O:9][N:8]=1.[OH-].[Na+]>CO.O1CCCC1>[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]([O:18][CH3:19])[CH:15]=[C:14]([C:20]([OH:22])=[O:21])[CH:13]=2)[O:9][N:8]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 9836338HCID 9836338, compound

Product 1

HCID 9814721HCID 9814721, compound

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

A stirred suspension of 3-(2-pyridyl)-5-(3-methoxycarbonyl-5-methoxyphenyl)-1,2,4-oxadiazole (191.3 mg, 0.62 mmol) in methanol-tetrahydrofuran (1:1, 10 mL) was treated with 1M sodium hydroxide (1.5 mL, 1.5 mmol). The reaction was stirred at 50° C. for 5 hours and the solvent then removed in vacuo. The residue was dissolved in a small amount of water and then acidified (pH 4-5) by the addition of 2 N hydrogen chloride. The precipitate was collected and dried to afford 131.8 (72%) of 3-(2-pyridyl)-5-(3-carboxy-5-methoxyphenyl)-1,2,4-oxadiazole: 1H NMR (DMSO): δ-8.81 (d, 1H), 8.28 (s, 1H), 8.21 (d, 1H), 8.06 (t, 1H), 7.88 (s, 1H), 7.74 (s, 1H), 7.65 (m, 1H), 3.95 (s, 3H).

Workup

  1. customthe solvent then removed in vacuo
  2. dissolutionThe residue was dissolved in a small amount of water
  3. additionby the addition of 2 N hydrogen chloride
  4. customThe precipitate was collected
  5. customdried

Sources & evidence

ORD record
ord-04997047e7174748b2f70cce83fa145d
Source dataset
uspto-grants-2003_12
Patent number
US06660753B2

Reaction notes

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