Ammonia → HCID 178419855, compound

HRID 869539Notes

Reaction equation

HRID 869539 reaction equation
[NH2:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[NH2:8].[CH:9]1([C:13](O)=O)[CH2:12][CH2:11][CH2:10]1.N>>[CH:9]1([C:13]2[NH:8][C:7]3[CH:6]=[CH:5][N:4]=[CH:3][C:2]=3[N:1]=2)[CH2:12][CH2:11][CH2:10]1

Participants

4

Reactant 3

HCID 222AmmoniaHCID 59183,4-DiaminopyridineHCID 19494Cyclobutanecarboxylic acid

Product 1

HCID 178419855HCID 178419855, compoundYield 73%

Conditions

Temperature
110 °C

Procedure

[step 1] 3,4-Diaminopyridine (2.0 g, 18.4 mmol) was mixed with polyphosphoric acid (20g), cyclobutanecarboxylic acid (2.63 mL, 27.5 mmol) was added, and the mixture was stirred with heating at 110° C. for 3 hr. The mixture was added dropwise to 5% aqueous ammonia solution under ice-cooling, and the mixture was extracted 3 times with chloroform. The combined organic layers were dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. To the obtained residue was added ethyl acetate (7 mL), and the precipitated crystals were collected by suction filtration to give 2-cyclobutyl-1H-imidazo[4,5-c]pyridine (2.3 g, 73%).

Workup

  1. additionwas added
  2. temperaturecooling
  3. extractionthe mixture was extracted 3 times with chloroform
  4. dry with materialThe combined organic layers were dried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. additionTo the obtained residue was added ethyl acetate (7 mL)
  7. filtrationthe precipitated crystals were collected by suction filtration

Sources & evidence

ORD record
ord-5f471ee2cd0847cab6ea2f1a2f6e34b4
Source dataset
uspto-grants-2015_03
Patent number
US08969345B2

Reaction notes

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