Pyridine → HCID 20144038, compound

HRID 648883Notes

Reaction equation

HRID 648883 reaction equation
[CH:1]1[CH:6]=[C:5]([CH:7]([OH:16])[C:8]([C:10]2[N:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[O:9])[N:4]=[CH:3][CH:2]=1.N1C=CC=CC=1.[C:23]([C:25]1[CH:33]=[CH:32][C:28]([C:29](Cl)=O)=[CH:27][CH:26]=1)#[N:24].ClCCl>C(#N)C>[C:23]([C:25]1[CH:33]=[CH:32][C:28]([CH2:29][O:9][CH:8]([C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][N:15]=2)[C:7]([C:5]2[CH:6]=[CH:1][CH:2]=[CH:3][N:4]=2)=[O:16])=[CH:27][CH:26]=1)#[N:24]

Participants

6

Reactant 4

HCID 1049PyridineHCID 6344DichloromethaneHCID 801724-Cyanobenzoyl chlorideHCID 95624α-Pyridoin

Product 1

HCID 20144038HCID 20144038, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To 2.14 g (0.01 mole) of α-pyridoin in 50 ml of acetonitrile was added 0.80 g (0.01 mole) of pyridine and then 1.65 g (0.01 mole) of p-cyanobenzoyl chloride portionwise with stirring. Stirring was continued for 1/2 hour. Then 150 ml of dichloromethane was added, the organic phase washed thoroughly with water, dried and evaporated to an oily solid residue. The residue was stirred with 80% hexane and 20% acetone to obtain a solid, 1.7 g (50%). After recrystallization from hexane-acetone, 0.9 g (53%), m.p., 152°-154° C., of NA-VI was recovered.

Workup

  1. washthe organic phase washed thoroughly with water
  2. customdried
  3. customevaporated to an oily solid residue
  4. stirringThe residue was stirred with 80% hexane and 20% acetone
  5. customto obtain a solid, 1.7 g (50%)
  6. customAfter recrystallization from hexane-acetone, 0.9 g (53%)
  7. customm.p., 152°-154° C., of NA-VI was recovered

Sources & evidence

ORD record
ord-56438169cbc84ff6ba4d7c1f315f0867
Source dataset
uspto-grants-1988_04
Patent number
US04737439

Reaction notes

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