Pyridine → HCID 54419924, compound

HRID 1741601Notes

Reaction equation

HRID 1741601 reaction equation
[CH2:1]([C:4]1[CH:5]=[C:6]([C:13]([OH:15])=[O:14])[C:7]([C:10]([OH:12])=O)=[N:8][CH:9]=1)[CH:2]=[CH2:3].C(OC(=O)C)(=O)C.N1C=CC=CC=1>COCCOC>[CH2:1]([C:4]1[CH:5]=[C:6]2[C:13](=[O:14])[O:15][C:10](=[O:12])[C:7]2=[N:8][CH:9]=1)[CH:2]=[CH2:3]

Participants

5

Reactant 3

HCID 1049PyridineHCID 7918Acetic Anhydride2×HCID 19010296HCID 19010296, compound

Product 1

HCID 54419924HCID 54419924, compound

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

A mixture of 7 g of crude 5-allylpyridine-2,3-dicarboxylic acid, 9.8 mL acetic anhydride, and 3.3 mL pyridine in 100 mL dry 1,2-dimethoxyethane is stirred under nitrogen and heated at 65° for 1 hour. After adding an additional 1 mL of acetic anhydride, the reaction is heated for 2 hours at 65°, then at reflux overnight. The reaction mixture is filtered, and the solids are washed with ether and ethyl acetate. The combined filtrates are concentrated in vacuo and reevaporated from xylenes to afford the product as a solid.

Workup

  1. temperatureheated at 65° for 1 hour
  2. temperaturethe reaction is heated for 2 hours at 65°
  3. temperatureat reflux overnight
  4. filtrationThe reaction mixture is filtered
  5. washthe solids are washed with ether and ethyl acetate
  6. concentrationThe combined filtrates are concentrated in vacuo
  7. customreevaporated from xylenes

Sources & evidence

ORD record
ord-5832fa21f81f4ed781c3d7bb1309f63d
Source dataset
uspto-grants-1994_08
Patent number
US05334576

Reaction notes

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