3-Pyridinemethanol → HCID 21426054, compound

HRID 258562Notes

Reaction equation

HRID 258562 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][OH:8])[CH:2]=1.[H-].[Na+].[H][H].[CH3:13][N:14]([C:18]1[CH:23]=[CH:22][C:21]([C:24]#[N:25])=[CH:20][CH:19]=1)[C:15](Cl)=[O:16]>O.COCCO>[CH3:13][N:14]([C:18]1[CH:23]=[CH:22][C:21]([C:24]#[N:25])=[CH:20][CH:19]=1)[C:15](=[O:16])[O:8][CH2:7][C:3]1[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=1

Participants

7

Reactant 4

HCID 75103-PyridinemethanolHCID 24758Sodium hydrideHCID 21426051HCID 21426051, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 21426054HCID 21426054, compoundYield 14.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 80192-MethoxyethanolSolvent2×

Procedure

To a solution of 3-pyridylcarbinol (4.3 g., 0.0392 mole) in 200 ml. of ethylene glycol monomethyl ether (glyme) was added a 57% dispersion of sodium hydride in oil (1.7 g., 0.0392 mole). After the exothermic reaction had subsided and the evolution of hydrogen had ceased, a solution of N-methyl-N-(4-cyanophenyl)carbamoyl chloride in 30 ml. of glyme was added dropwise. A suspension formed and was stirred at room temperature for 18 hrs. The reaction mixture was poured into 700 ml. of water. The reaction product was extracted with methylene dichloride and the extract was dried over magnesium sulfate and concentrated. The residue was an oil which solidified. This was recrystallized from hexane to give 1.5 g. of solid melting at 82°-84.5° C. This solid is a 14.4% yield of 3-pyridylmethyl N-methyl-N-(4-cyanophenyl)carbamate.

Workup

  1. customAfter the exothermic reaction
  2. customA suspension formed
  3. additionThe reaction mixture was poured into 700 ml
  4. extractionThe reaction product was extracted with methylene dichloride
  5. dry with materialthe extract was dried over magnesium sulfate
  6. concentrationconcentrated
  7. customThis was recrystallized from hexane
  8. customto give 1.5 g

Sources & evidence

ORD record
ord-9812e4869dc648648ed5e67068f14b41
Source dataset
uspto-grants-1977_07
Patent number
US04033972

Reaction notes

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