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

HRID 848212Notes

Reaction equation

HRID 848212 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-fd962f039f2b49eaa56712343fad21d4
Source dataset
uspto-grants-1981_10
Patent number
US04294969

Reaction notes

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