2,3-Diaminopyridine → HCID 178456120, compound

HRID 2054442Notes

Reaction equation

HRID 2054442 reaction equation
[NH2:1][C:2]1[C:7]([NH2:8])=[CH:6][CH:5]=[CH:4][N:3]=1.[Cl:9][CH:10]([CH3:13])[C:11]#N>O>[Cl:9][CH:10]([C:13]1[NH:1][C:2]2=[N:3][CH:4]=[CH:5][CH:6]=[C:7]2[N:8]=1)[CH3:11]

Participants

4

Reactant 2

HCID 99562,3-DiaminopyridineHCID 5192252-Chloropropionitrile

Product 1

HCID 178456120HCID 178456120, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

5.2 g of 2,3-diaminopyridine in 209 g of polyphosphoric acid are heated at 120° C. for 0.5 h. The solution is cooled to 80° C. and 4.6 ml of 2-chloropropionitrile are added. Thereafter, the reaction mixture is heated to 180° C. for 2.5 h. After cooling, the polyphosphoric acid is hydrolyzed with water, the mixture is filtered using charcoal and celite and the pH value of the filtrate is adjusted to pH 4 using 9 M aqueous sodium hydroxide solution. The mixture is extracted twice each with 250 ml of ethyl acetate, the combined organic phases are dried using sodium sulfate, concentrated and lyophilized from ethanol/water to give 3.56 g of the title compound as a light brown, amorpheous solid. M.p. 132° C. TLC: Rf=0.60 (dichloromethane/methanol 8:1).

Workup

  1. temperatureThereafter, the reaction mixture is heated to 180° C. for 2.5 h
  2. temperatureAfter cooling
  3. filtrationthe mixture is filtered
  4. extractionThe mixture is extracted twice each with 250 ml of ethyl acetate
  5. customthe combined organic phases are dried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-896544e15be7411d9528a09bbe7c4d6e
Source dataset
uspto-grants-2008_02
Patent number
US07329677B2

Reaction notes

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