Phenylacetic Acid → HCID 53748754, compound

HRID 868360Notes

Reaction equation

HRID 868360 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH:7]=O)[CH:2]=1.[C:9]1([CH2:15][C:16]([OH:18])=[O:17])[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.C(OC(=O)C)(=O)C.C(=O)(O)[O-].[Na+]>C(N(CC)CC)C>[C:9]1([C:15](=[CH:7][C:3]2[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=2)[C:16]([OH:18])=[O:17])[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

6

Reactant 4

HCID 999Phenylacetic AcidHCID 7918Acetic AnhydrideHCID 103713-PyridinecarboxaldehydeHCID 516892Sodium Bicarbonate

Product 1

HCID 53748754HCID 53748754, compoundYield 30.2%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

To a mixture of 4.3 g of 3-pyridinecarbaldehyde, 5.4 g of phenylacetic acid, and 11.4 ml of acetic anhydride, 5.6 g of triethylamine is added with stirring, and the mixture is stirred at 100° C. for 4 hours. The reaction mixture is alkalified with 10% aqueous sodium bicarbonate solution. The aqueous solution is warmed and filtered. The filtrate is adjusted to pH 4.5 with 10% hydrochloric acid, and the resulting precipitate is collected and recrystallized from ethanol to give 2.7 g of the title compound, m.p. 190°-192° C.

Workup

  1. additionis added
  2. stirringthe mixture is stirred at 100° C. for 4 hours
  3. temperatureThe aqueous solution is warmed
  4. filtrationfiltered
  5. customthe resulting precipitate is collected
  6. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-86bab2b9bc054a52bb4d178f1d6a618a
Source dataset
uspto-grants-1988_10
Patent number
US04778796

Reaction notes

Loading…