Imidazole → HCID 20532704, compound

HRID 904141Notes

Reaction equation

HRID 904141 reaction equation
[CH3:1][N:2]([CH2:4][C:5]1[C:10]([OH:11])=[CH:9][CH:8]=[CH:7][N:6]=1)[CH3:3].[NH:12]1C=CN=[CH:13]1>C1(C)C(C)=CC=CC=1>[N:2]1([CH2:4][C:5]2[C:10]([OH:11])=[CH:9][CH:8]=[CH:7][N:6]=2)[CH:1]=[CH:13][N:12]=[CH:3]1

Participants

4

Reactant 2

HCID 795ImidazoleHCID 751082-((Dimethylamino)methyl)pyridin-3-ol

Product 1

HCID 20532704HCID 20532704, compoundYield 71.2%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

A solution consisting of 2-dimethylaminomethyl-3-hydroxypyridine (30.4 g.) and imidazole (13.6 g.) dissolved in xylene (100 ml.) was heated under reflux for a period of five hours and then allowed to cool to room temperature (~25° C.). The resulting precipitated oil was then scratched so as to induce crystallization and the solid product so obtained was thereafter crystallized from isopropanol/petroleum ether (b.p. 60°-80° C.) to afford pure 2-(imidazol-1-ylmethyl)-3-hydroxypyridine (yield, 24.9 g.), m.p. 154°-155° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for a period of five hours
  3. customThe resulting precipitated oil
  4. customcrystallization
  5. customthe solid product so obtained
  6. customwas thereafter crystallized from isopropanol/petroleum ether (b.p. 60°-80° C.)

Sources & evidence

ORD record
ord-d85037c91bc0498fa18a33cbcd1ab125
Source dataset
uspto-grants-1980_10
Patent number
US04230714

Reaction notes

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