Hippuric Acid → HCID 1945690, compound

HRID 2278350Notes

Reaction equation

HRID 2278350 reaction equation
[C:1]([OH:13])(=[O:12])[CH2:2][NH:3][C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=O.[CH:14]1[CH:19]=[C:18]2[CH:20]=[CH:21][CH:22]=[C:23]([CH:24]=O)[C:17]2=[CH:16][CH:15]=1.C([O-])(=O)C.[Na+]>C(OC(=O)C)(=O)C>[C:23]1(/[CH:24]=[C:2]2\[N:3]=[C:4]([C:6]3[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=3)[O:13][C:1]\2=[O:12])[C:17]2[C:18](=[CH:19][CH:14]=[CH:15][CH:16]=2)[CH:20]=[CH:21][CH:22]=1

Participants

5

Reactant 3

HCID 464Hippuric AcidHCID 61951-NaphthaldehydeHCID 517045Sodium Acetate

Product 1

HCID 1945690HCID 1945690, compound

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Conditions

Temperature
80 °C

Procedure

A solution of hippuric acid (4.0 g, 1.0 eq.) was added to a solution acetic anhydride (10 mL), 1-naphthylaldehyde (3.84 g, 1.1 eq.) and sodium acetate (2.21 g, 1.2 eq.). The reaction mixture was then heated at 80° C. for 2 hours, then cooled to room temperature, filtered, and washed with acetic anhydride. After air drying, the solid was washed back with water and air-dried overnight to give the desired compound.

Workup

  1. temperaturecooled to room temperature
  2. filtrationfiltered
  3. washwashed with acetic anhydride
  4. customAfter air drying
  5. washthe solid was washed back with water
  6. customair-dried overnight

Sources & evidence

ORD record
ord-44ea16d5da1a4557a9bbc6ec986a0cf1
Source dataset
uspto-grants-2015_09
Patent number
US09133157B2

Reaction notes

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