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

HRID 1074609Notes

Reaction equation

HRID 1074609 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-6c6e347bbdf245f6833ad47ad5a62d2a
Source dataset
uspto-grants-1983_07
Patent number
US04393212

Reaction notes

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