Ethylene carbonate → 3-(2-Hydroxyethyl)-2-methylimidazo[4,5-c]pyridine

HRID 232034Notes

Reaction equation

HRID 232034 reaction equation
[CH3:1][C:2]1[NH:3][C:4]2[CH:9]=[CH:8][N:7]=[CH:6][C:5]=2[N:10]=1.C1(=O)O[CH2:14][CH2:13][O:12]1>>[OH:12][CH2:13][CH2:14][N:10]1[C:5]2[CH:6]=[N:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[CH3:1]

Participants

3

Reactant 2

HCID 7303Ethylene carbonateHCID 178432317HCID 178432317, compound

Product 1

HCID 200308243-(2-Hydroxyethyl)-2-methylimidazo[4,5-c]pyridineYield 9%

Conditions

Temperature
150 °C

Procedure

2-Methylimidazo[4,5-c]pyridine (10.6 g) was mixed with ethylene carbonate (8.3 g) and heated as a melt at 150° C. for 1/2 hour. The crude black product was chromatographed on silica eluting with 40% methanol in ethyl acetate. The fraction with Rf 0.33 in methanol, ethyl acetate, (2:3) was evaporated and was identified as a mixture of the title compound and of the isomeric 1-(2-hydroxyethyl)-2-methylimidazo[4,5-c]pyridine. The mixture was chromatographed on silica eluting with 20% methanol in acetone. Fractions containing the more mobile isomer were combined and evaporated yielding the title compound (1.22 g, 9%) as a foam.

Workup

  1. customThe crude black product was chromatographed on silica eluting with 40% methanol in ethyl acetate
  2. customThe fraction with Rf 0.33 in methanol, ethyl acetate, (2:3) was evaporated
  3. additionwas identified as a mixture of the title compound and of the isomeric 1-(2-hydroxyethyl)-2-methylimidazo[4,5-c]pyridine
  4. customThe mixture was chromatographed on silica eluting with 20% methanol in acetone
  5. additionFractions containing the more mobile isomer
  6. customevaporated

Sources & evidence

ORD record
ord-3bcb2be2d0514a2dbfe62c58f6c9a0af
Source dataset
uspto-grants-1989_07
Patent number
US04851412

Reaction notes

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