Piperidine → Benzoic Acid

HRID 1645258Notes

Reaction equation

HRID 1645258 reaction equation
N1C2C(=CC=CC=2)CC1=O.C(C1OC=C([C:18]2[CH:19]=[C:20]([CH:25]=[CH:26][CH:27]=2)[C:21]([O:23]C)=[O:22])C=1)=O.N1CCCCC1>CCO>[C:21]([OH:23])(=[O:22])[C:20]1[CH:25]=[CH:26][CH:27]=[CH:18][CH:19]=1

Participants

5

Reactant 3

HCID 8082PiperidineHCID 321710OxindoleHCID 86639089HCID 86639089, compound

Product 1

HCID 243Benzoic AcidYield 184.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of oxindole (400 mg, 2.4 mmol), methyl 3-(5-formylfuran-3-yl)benzoate (518 mg, 2.4 mmol) and piperidine (0.24 mL, 2.4 mmol) in EtOH (10 mL) was stirred at rt 30 min. The resulting precipitate was collected by filtration to yield desired (E)-3-(5-chloro-2-oxoindolin-3-ylidene)methyl)furan-2-yl)benzoic acid (541 mg). LCMS (ES): m/z 366 [M+1]+.

Workup

  1. filtrationThe resulting precipitate was collected by filtration

Sources & evidence

ORD record
ord-f6a4741681c14740bb9d75dc2995a967
Source dataset
uspto-grants-2012_02
Patent number
US08124649B2

Reaction notes

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