Methanol → HCID 69003606, compound

HRID 1821368Notes

Reaction equation

HRID 1821368 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH:10]=[CH:11][C:12]2[CH:22]=[CH:21][CH:20]=[CH:19][C:13]=2/[C:14](/[NH:17][OH:18])=[N:15]\[H])=[N:2]1.CC[C:25]([C:27](Cl)=[O:28])=O.C[OH:31].[OH-].[Na+]>N1C=CC=CC=1>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3](/[CH:10]=[CH:11]/[C:12]2[CH:22]=[CH:21][CH:20]=[CH:19][C:13]=2[C:14]2[N:15]=[C:25]([C:27]([OH:28])=[O:31])[O:18][N:17]=2)=[N:2]1

Participants

6

Reactant 4

HCID 887MethanolHCID 14798Sodium HydroxideHCID 11007880Butanoyl chloride, 2-oxo-HCID 178506493HCID 178506493, compound

Product 1

HCID 69003606HCID 69003606, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
90 °C

Procedure

(E)-2-[2-(1H-indazol-3-yl)vinyl]-N-hydroxybenzamidine (0.17 g, 0.60 mmol) was dissolved in pyridine (5.0 mL) and ethyloxalyl chloride (0.12 mL, 1.1 mmol) was added thereto, followed by stirring at 90° C. for 2 hours. Methanol and 2 mol/L aqueous sodium hydroxide solution were added to the mixture and the organic layer was extracted with ethyl acetate. The aqueous layer was neutralized by 6 mol/L hydrochloric acid and the precipitated solid was collected by filtration and then dried. The obtained solid was triturated in ethanol to obtain (E)-3-{2-[2-(1H-indazol-3-yl)vinyl]phenyl}[1,2,4]oxadiazole-5-carboxylic acid (0.12 g, 50%).

Workup

  1. extractionthe organic layer was extracted with ethyl acetate
  2. filtrationthe precipitated solid was collected by filtration
  3. customdried
  4. customThe obtained solid was triturated in ethanol

Sources & evidence

ORD record
ord-b23782a5532741b392f51b24d8c30cfe
Source dataset
uspto-grants-2009_10
Patent number
US07605272B2

Reaction notes

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