Pyridine → HCID 5388546, compound

HRID 1576381Notes

Reaction equation

HRID 1576381 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=O.[C:10]([CH2:12]C(O)=O)#[N:11].N1C=CC=CC=1>C(O)(C)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)/[CH:5]=[CH:12]/[C:10]#[N:11]

Participants

5

Reactant 3

HCID 1049PyridineHCID 9740Cyanoacetic acidHCID 114773-Chlorobenzaldehyde

Product 1

HCID 5388546HCID 5388546, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

m-Chlorobenzaldehyde (210.75 g; 1.5 m), cyanoacetic acid (127.5 g; 1.5 m) and pyridine (150 ml.) were refluxed for two days. The solution was evaporated to give an oil which was distilled to give a mixture of isomers (72% trans/23% cis; 5% aldehyde), Yield (129 g; 53%), b.p. 70°-85°C. at 0.8 mm. The material was dissolved in isopropanol and allowed to fractionally crystallise at 0°C. The solid was filtered and freeze-dried. Yield of pure trans isomer was 15 g (6.1%) b.p. 104°-106°C. at 1 mm; m.p. 26°-28°C.

Workup

  1. customThe solution was evaporated
  2. customto give an oil which
  3. distillationwas distilled
  4. customto give
  5. customYield (129 g; 53%), b.p. 70°-85°C. at 0.8 mm
  6. customto fractionally crystallise at 0°C
  7. filtrationThe solid was filtered
  8. customfreeze-dried

Sources & evidence

ORD record
ord-87623bbc97324f6393e29ecb8b9658fc
Source dataset
uspto-grants-1976_09
Patent number
US03980785

Reaction notes

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