Imidazole → HCID 88775180, compound

HRID 904150Notes

Reaction equation

HRID 904150 reaction equation
Cl.CN([CH2:5][C:6]1[CH:11]=[CH:10][C:9]([OH:12])=[C:8]([Cl:13])[N:7]=1)C.[OH-].[Na+].[NH:16]1[CH:20]=[CH:19][N:18]=[CH:17]1>O.C1(C)C(C)=CC=CC=1>[NH:16]1[CH:20]=[CH:19][N:18]=[C:17]1[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([OH:12])=[C:8]([Cl:13])[N:7]=1

Participants

6

Reactant 3

HCID 795ImidazoleHCID 14798Sodium HydroxideHCID 23333781HCID 23333781, compound

Product 1

HCID 88775180HCID 88775180, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 7237O-XyleneSolvent

Procedure

This hydrochloride was dissolved in water and the solution was neutralised with dilute sodium hydroxide solution and evaporated. The residue was extracted several times with hot toluene and the combined extracts were filtered and evaporated to give the corresponding free base. The base (3.70 g) and imidazole (1.5 g) were heated under reflux in xylene (50 ml) for 3 hours. The mixture was then evaporated and the resulting dark residue was extracted several times with hot water. The aqueous solution was evaporated and the residue was crystallised first from ethyl acetate and then from water to give 2-(1-imidazolylmethyl)-5-hydroxy-6-chloropyridine (0.88 g), m.p. 157°-158°.

Workup

  1. customevaporated
  2. extractionThe residue was extracted several times with hot toluene
  3. filtrationthe combined extracts were filtered
  4. customevaporated
  5. customto give the corresponding free base
  6. customThe mixture was then evaporated
  7. extractionthe resulting dark residue was extracted several times with hot water
  8. customThe aqueous solution was evaporated
  9. customthe residue was crystallised first from ethyl acetate

Sources & evidence

ORD record
ord-4f74d14507244834ad00db839d989fa0
Source dataset
uspto-grants-1980_10
Patent number
US04230714

Reaction notes

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