3-Pyridinecarboxaldehyde → HCID 4052667, compound

HRID 745755Notes

Reaction equation

HRID 745755 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([CH2:6][C:7]#[N:8])=[CH:4][CH:3]=1.[N:11]1[CH:16]=[CH:15][CH:14]=[C:13]([CH:17]=O)[CH:12]=1.[Na]>C(O)C>[C:7]([C:6]([C:5]1[CH:9]=[CH:10][C:2]([Cl:1])=[CH:3][CH:4]=1)=[CH:17][C:13]1[CH:12]=[N:11][CH:16]=[CH:15][CH:14]=1)#[N:8]

Participants

5

Reactant 3

HCID 103713-PyridinecarboxaldehydeHCID 2415824-Chlorobenzyl cyanideHCID 5360545Sodium

Product 1

HCID 4052667HCID 4052667, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A solution of 4-chlorobenzyl cyanide (7.58 g) and pyridine-3-aldehyde (5.35 g) in absolute ethanol (50 ml) was warmed to 50° C.; 3.5 ml of a solution of sodium (2.74 g) in absolute ethanol (32 ml) was added and the mixture was left without further heating. After 1 hour, the solid product was filtered off, washed with ethanol, and then diethylether, and dried. Recrystallization of this material from ethanol (150 ml) with charcoal treatment gave 4 in 48% yield as pale yellow needles; m.p. 141°-143° C.

Workup

  1. waitthe mixture was left without further heating
  2. filtrationthe solid product was filtered off
  3. washwashed with ethanol
  4. dry with materialdiethylether, and dried
  5. customRecrystallization of this material from ethanol (150 ml) with charcoal treatment
  6. customgave 4 in 48% yield as pale yellow needles

Sources & evidence

ORD record
ord-f930edcd24ce43d9959cffdc0839215b
Source dataset
uspto-grants-1986_07
Patent number
US04600712

Reaction notes

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