Pyridine → HCID 57098744, compound

HRID 2394488Notes

Reaction equation

HRID 2394488 reaction equation
Cl[C:2]([O:4][CH2:5][CH3:6])=[O:3].[OH:7][CH2:8][CH2:9][NH:10][N:11]=[CH:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.N1C=CC=CC=1>C(OCC)(=O)C>[OH:7][CH2:8][CH2:9][N:10]([C:2]([O:4][CH2:5][CH3:6])=[O:3])[N:11]=[CH:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 10928Ethyl chloroformateHCID 70531719HCID 70531719, compound

Product 1

HCID 57098744HCID 57098744, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

This acylation is performed in the following manner: 1.08 g (10-2 moles) of ethyl chloroformate in 5 ml of anhydrous ethyl acetate are added dropwise to a solution containing 10-2 moles of benzaldehyde (2-hydroxyethyl)hydrazone and 0.79 g (10-2 moles) of anhydrous pyridine in 20 ml of anhydrous ethyl acetate, with stirring in the cold. The reaction mixture is left at 0° C. with stirring for 2 hours and then it is filtered. The product obtained is washed with 10 ml of water and then dried and recrystallized from a mixture of ethyl acetate and petroleum ether. It has a melting point of 69.5° C. The reaction yield is 62%.

Workup

  1. waitThe reaction mixture is left at 0° C.
  2. stirringwith stirring for 2 hours
  3. filtrationit is filtered
  4. customThe product obtained
  5. washis washed with 10 ml of water
  6. customdried
  7. customrecrystallized from a mixture of ethyl acetate and petroleum ether
  8. customThe reaction yield is 62%

Sources & evidence

ORD record
ord-b1ac80edb219463ea56942746b2e53c3
Source dataset
uspto-grants-1998_09
Patent number
US05811456

Reaction notes

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