2,5-Dimethoxytetrahydrofuran → 2-chloro-3-pyrrol-1-ylpyridine

HRID 614328Notes

Reaction equation

HRID 614328 reaction equation
[Cl:1][C:2]1[C:7]([NH2:8])=[CH:6][CH:5]=[CH:4][N:3]=1.CO[CH:11]1[CH2:15][CH2:14][CH:13](OC)O1>C(O)(=O)C>[Cl:1][C:2]1[C:7]([N:8]2[CH:11]=[CH:15][CH:14]=[CH:13]2)=[CH:6][CH:5]=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 790982,5-DimethoxytetrahydrofuranHCID 805282-Chloro-3-pyridylamine

Product 1

HCID 27579082-chloro-3-pyrrol-1-ylpyridineYield 75%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of acetic acid (25 ml), 2-chloro-3-aminopyridine (5.1 g, 0.04 m) and 2,5-dimethoxytetrahydrofuran (0.05 m) was heated to reflux. After two hours, the mixture was concentrated to dryness, treated with ice and neutralized with saturate Na2CO3 solution. The aqueous layer was extracted with CHCl3 (3×100 ml). The organic extract was dried over Na2SO4, filtered and concentrated to dryness. The residue was distilled to yield 5.3 g (75% yield) of 2-chloro-3-(1-pyrrolyl) pyridine; b.p=95°-100° at 0.5 mm.

Workup

  1. concentrationthe mixture was concentrated to dryness
  2. additiontreated with ice and neutralized with saturate Na2CO3 solution
  3. extractionThe aqueous layer was extracted with CHCl3 (3×100 ml)
  4. extractionThe organic extract
  5. dry with materialwas dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated to dryness
  8. distillationThe residue was distilled

Sources & evidence

ORD record
ord-32c4a8437d274ca7afb03a459bfa139a
Source dataset
uspto-grants-1979_03
Patent number
US04144343

Reaction notes

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