Hippuric Acid → HCID 68543765, compound

HRID 1442580Notes

Reaction equation

HRID 1442580 reaction equation
C(OC(=O)C)(=O)C.[C:8]([C:10]1[CH:11]=[C:12]([CH:15]=[CH:16][CH:17]=1)[CH:13]=O)#[N:9].[C:18]([OH:30])(=[O:29])[CH2:19][NH:20][C:21]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=O.C([O-])(=O)C.[Na+]>C(OCC)(=O)C.O.C(OCC)C>[O:29]=[C:18]1[O:30][C:21]([C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)=[N:20][C:19]1=[CH:13][C:12]1[CH:11]=[C:10]([CH:17]=[CH:16][CH:15]=1)[C:8]#[N:9]

Participants

7

Reactant 4

HCID 464Hippuric AcidHCID 7918Acetic AnhydrideHCID 90670m-FormylbenzonitrileHCID 517045Sodium Acetate

Product 1

HCID 68543765HCID 68543765, compoundYield 74%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 22728543Water ethylacetateSolvent

Procedure

An acetic anhydride suspension (10 mL) of 3-cyanobenzaldehyde (1.32 g, 10.1 mmol), hippuric acid (1.81 g, 10.1 mmol) and sodium acetate (826 mg, 10.1 mmol) was stirred at 100° C. for 30 minutes. After the reaction mixture was allowed to cool and diethyl ether was added thereto, the solid was taken out by filtration and the filtrate was concentrated under reduced pressure. The solid obtained and the residue were combined and the mixture was suspended in a mixture of ethyl acetate-water. After filtering, the solid was dissolved in dichloromethane, followed by washing with water. The mixture was dried over sodium sulfate, filtered and concentrated under reduced pressure to give the title compound (2.04 g, 74%).

Workup

  1. temperatureto cool
  2. filtrationthe solid was taken out by filtration
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customThe solid obtained
  5. filtrationAfter filtering
  6. dissolutionthe solid was dissolved in dichloromethane
  7. washby washing with water
  8. dry with materialThe mixture was dried over sodium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-c332bbc5afae4a34b9811d9716a5994e
Source dataset
uspto-grants-2010_02
Patent number
US07659267B2

Reaction notes

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