Glutaric anhydride → HCID 2812221, compound

HRID 2272568Notes

Reaction equation

HRID 2272568 reaction equation
[O:1]1[C:6](=[O:7])[CH2:5][CH2:4][CH2:3][C:2]1=[O:8].[NH2:9][C:10]1[CH:17]=[CH:16][C:13]([C:14]#[N:15])=[CH:12][CH:11]=1>C1COCC1>[C:14]([C:13]1[CH:16]=[CH:17][C:10]([NH:9][C:2](=[O:8])[CH2:3][CH2:4][CH2:5][C:6]([OH:1])=[O:7])=[CH:11][CH:12]=1)#[N:15]

Participants

4

Reactant 2

HCID 7940Glutaric anhydrideHCID 133964-Aminobenzonitrile

Product 1

HCID 2812221HCID 2812221, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of dihydro-2H-pyran-2,6(3H)-dione (483 mg, 4.23 mmol) and 4-aminobenzonitrile (500 mg, 4.23 mmol) in THF (15 mL) was heated with reflux for 14 hr. The reaction solution was concentrated under reduced pressure, and the precipitate was washed with ethyl acetate to give 5-(4-cyanophenylamino)-5-oxopentanoic acid (782 mg, 3.37 mmol, 80%) as a pale-yellow powder.

Workup

  1. temperaturewith reflux for 14 hr
  2. concentrationThe reaction solution was concentrated under reduced pressure
  3. washthe precipitate was washed with ethyl acetate

Sources & evidence

ORD record
ord-908efa9cc8444d8f912fb10589af4386
Source dataset
uspto-grants-2015_09
Patent number
US09120776B2

Reaction notes

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