Acetic Acid → 2-chloro-3-pyrrol-1-ylpyridine

HRID 2427092Notes

Reaction equation

HRID 2427092 reaction equation
C(O)(=O)C.[Cl:5][C:6]1[C:11]([NH2:12])=[CH:10][CH:9]=[CH:8][N:7]=1.CO[CH:15]1[CH2:19][CH2:18][CH:17](OC)O1>O>[Cl:5][C:6]1[C:11]([N:12]2[CH:15]=[CH:19][CH:18]=[CH:17]2)=[CH:10][CH:9]=[CH:8][N:7]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 790982,5-DimethoxytetrahydrofuranHCID 805282-Chloro-3-pyridylamine

Product 1

HCID 27579082-chloro-3-pyrrol-1-ylpyridineYield 93.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 30 ml of acetic acid were added 5.0 g of 2-chloro-3-pyridinylamine and 5.6 g of 2,5-dimethoxytetrahydrofuran, and the mixture was heated to reflux for 2 hours. The reaction mixture was allowed to cool to room temperature, poured into water, and then extracted with ethyl acetate two times. The organic layers were combined, washed successively with water and an aqueous saturated sodium chloride solution, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The resulting residue was subjected to silica gel chromatography to obtain 6.5 g of 1-(2-chloro-3-pyridinyl)-1H-pyrrole of the formula:

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 2 hours
  3. extractionextracted with ethyl acetate two times
  4. washwashed successively with water
  5. dry with materialan aqueous saturated sodium chloride solution, dried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-55f8504b34564a6d9ffacbca3b10db52
Source dataset
uspto-grants-2011_06
Patent number
US07968573B2

Reaction notes

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