Ethanol → HCID 14390475, compound

HRID 623091Notes

Reaction equation

HRID 623091 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[N:18]([CH2:19][C:20]([OH:22])=[O:21])[C:13]3=[N:14][CH:15]=[CH:16][CH:17]=[C:12]3[N:11]=2)=[CH:6][CH:5]=1)([O-:3])=[O:2].S(=O)(=O)(O)O.[CH2:28](O)[CH3:29]>>[CH2:28]([O:21][C:20](=[O:22])[CH2:19][N:18]1[C:13]2=[N:14][CH:15]=[CH:16][CH:17]=[C:12]2[N:11]=[C:10]1[C:7]1[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:9][CH:8]=1)[CH3:29]

Participants

4

Reactant 3

HCID 702Ethanol2×HCID 1118Sulfuric AcidHCID 14390459HCID 14390459, compound

Product 1

HCID 14390475HCID 14390475, compoundYield 71%

Procedure

A suspension of crude 2-(4-nitrophenyl)-3H-imidazo[4,5-b]pyridine-3-acetic acid (1.5 g, 0.00503 mole) in absolute ethanol was acidified with 0.5 ml of concentrated sulfuric acid and refluxed under nitrogen for three days. The solution was evaporated to approximately one-third of its original volume (reduced pressure), and saturated sodium bicarbonate solution and ethyl acetate were added. The layers were separated, the aqueous layer was re-extracted with ethyl acetate and the combined organic layers were washed twice with water, dried over sodium sulfate, filtered, and evaporated under reduced pressure to give a solid. The solid was dissolved in hot absolute ethanol and filtered hot. Upon cooling to room temperature, a solid formed which was collected by filtration, rinsed with water, and dried under high vacuum at 50° C. overnight to give 1.17 g (71%) of title compound, mp 191.5°-193.5° C.

Workup

  1. temperaturerefluxed under nitrogen for three days
  2. customThe solution was evaporated to approximately one-third of its original volume (reduced pressure), and saturated sodium bicarbonate solution and ethyl acetate
  3. additionwere added
  4. customThe layers were separated
  5. extractionthe aqueous layer was re-extracted with ethyl acetate
  6. washthe combined organic layers were washed twice with water
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. customevaporated under reduced pressure
  10. customto give a solid
  11. filtrationfiltered hot
  12. customa solid formed which
  13. filtrationwas collected by filtration
  14. washrinsed with water
  15. customdried under high vacuum at 50° C. overnight

Sources & evidence

ORD record
ord-0dbcf138eb5e4a3fabe2578077b594c2
Source dataset
uspto-grants-1988_09
Patent number
US04772600

Reaction notes

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