2,5-Dimethoxytetrahydrofuran → 2-Chloro-5-(1-pyrrolyl)nicotinonitrile

HRID 1277946Notes

Reaction equation

HRID 1277946 reaction equation
[NH2:1][C:2]1[CH:3]=[N:4][C:5]([Cl:10])=[C:6]([CH:9]=1)[C:7]#[N:8].CO[CH:13]1[CH2:17][CH2:16][CH:15](OC)O1>C(OC(=O)C)(=O)C>[Cl:10][C:5]1[N:4]=[CH:3][C:2]([N:1]2[CH:13]=[CH:17][CH:16]=[CH:15]2)=[CH:9][C:6]=1[C:7]#[N:8]

Participants

4

Reactant 2

HCID 790982,5-DimethoxytetrahydrofuranHCID 204962095-Amino-2-chloropyridine-3-carbonitrile

Product 1

HCID 129197522-Chloro-5-(1-pyrrolyl)nicotinonitrileYield 78.4%

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Procedure

A solution of 5-amino-2-chloronicotinonitrile (5.0 g, 0.033 m), 2,5-dimethoxytetrahydrofuran (11 g, 0.085 m) and acetic anhydride (20 ml) was heated at reflux with stirring. After two hours, the solution was concentrated to dryness under reduced pressure (20 mm). The residue was triturated with CCl4 and filtered to yield 5.2 g (78% yield) of 2-chloro-5-(1-pyrrolyl)nicotinonitrile, m.p.=144°-146°.

Workup

  1. temperatureat reflux
  2. concentrationthe solution was concentrated to dryness under reduced pressure (20 mm)
  3. customThe residue was triturated with CCl4
  4. filtrationfiltered

Sources & evidence

ORD record
ord-a49ac716b8d64ac8bd749f1616c64a96
Source dataset
uspto-grants-1981_07
Patent number
US04279913

Reaction notes

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