Methanol → HCID 178498387, compound

HRID 1896450Notes

Reaction equation

HRID 1896450 reaction equation
[N:1]1[C:9]2[C:4](=[N:5][CH:6]=[CH:7][C:8]=2[C:10]([OH:12])=[O:11])[NH:3][CH:2]=1.OS(O)(=O)=O.[CH3:18]O>>[N:1]1[C:9]2[C:4](=[N:5][CH:6]=[CH:7][C:8]=2[C:10]([O:12][CH3:18])=[O:11])[NH:3][CH:2]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 178524549HCID 178524549, compound

Product 1

HCID 178498387HCID 178498387, compoundYield 80%

Procedure

Absolute methanol (30 ml) is added to acid x177 (2.0 g). Concentrated H2SO4 (4 ml) is added to the obtained suspension at 0° C. The reaction mixture is refluxed under protection from the air moisture and vigorous stirring for 10 h. After 3 h the solid is completely dissolved. The next morning the reaction mixture is evaporated to half-volume in the vacuum of a rotary evaporator and neutralized under cooling with ice with aqueous ammonia to pH 8-9. The formed precipitate is quickly separated by filtration, washed with ice-cold water (2×30 ml), and dried over P2O5 overnight to afford 1.74 g of methyl 3H-imidazo[4,5-b]pyridine-7-carboxylate x179.

Workup

  1. temperatureThe reaction mixture is refluxed under protection from the air moisture
  2. dissolutionAfter 3 h the solid is completely dissolved
  3. customThe next morning the reaction mixture is evaporated to half-volume in the vacuum of a rotary evaporator
  4. temperatureunder cooling with ice with aqueous ammonia to pH 8-9
  5. customThe formed precipitate is quickly separated by filtration
  6. washwashed with ice-cold water (2×30 ml)
  7. dry with materialdried over P2O5 overnight

Sources & evidence

ORD record
ord-5105645055d9412888c804f73b8a86a4
Source dataset
uspto-grants-2013_08
Patent number
US08518943B2

Reaction notes

Loading…