2,5-Dimethoxytetrahydrofuran → 2-Chloro-6-(1H-pyrrol-1-yl)benzonitrile

HRID 1270081Notes

Reaction equation

HRID 1270081 reaction equation
[NH2:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([Cl:10])[C:3]=1[C:4]#[N:5].CO[CH:13]1[CH2:17][CH2:16][CH:15](OC)O1.Cl.ClC1C=CN=CC=1>O1CCOCC1>[Cl:10][C:6]1[C:3]([C:4]#[N:5])=[C:2]([N:1]2[CH:13]=[CH:17][CH:16]=[CH:15]2)[CH:9]=[CH:8][CH:7]=1

Participants

5

Reactant 3

HCID 790982,5-DimethoxytetrahydrofuranHCID 810562-Amino-6-chlorobenzonitrileHCID 818524-Chloropyridine hydrochloride

Product 1

HCID 6087322-Chloro-6-(1H-pyrrol-1-yl)benzonitrileYield 87.8%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of 2-amino-6-chloro-benzonitrile (30 g), 2,5-dimethoxytetrahydrofuran (30 g) and 4-chloropyridine hydrochloride (17 g) in dioxane was heated to 70° C. for 2.5 h. The solvent was evaporated in vacuo. Dichloromethane was then added to the residue and the spent 4-chloropyridine hydrochloride filtered off. The dichloromethane was evaporated in vacuo to give 1-(3′chloro-2′-cyanophenyl)pyrrole (35 g)

Workup

  1. customThe solvent was evaporated in vacuo
  2. additionDichloromethane was then added to the residue
  3. filtrationthe spent 4-chloropyridine hydrochloride filtered off
  4. customThe dichloromethane was evaporated in vacuo

Sources & evidence

ORD record
ord-01fa8400f3c247c68f02e9bdb1e7435d
Source dataset
uspto-grants-2007_04
Patent number
US07202240B2

Reaction notes

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