2,3-Diaminopyridine → HCID 178448403, compound

HRID 2054443Notes

Reaction equation

HRID 2054443 reaction equation
[NH2:1][C:2]1[C:7]([NH2:8])=[CH:6][CH:5]=[CH:4][N:3]=1.[Cl:9][CH:10]([CH2:14][CH3:15])[C:11](O)=O>O>[Cl:9][CH:10]([C:11]1[NH:1][C:2]2=[N:3][CH:4]=[CH:5][CH:6]=[C:7]2[N:8]=1)[CH2:14][CH3:15]

Participants

4

Reactant 2

HCID 99562,3-DiaminopyridineHCID 201372-Chlorobutyric acid

Product 1

HCID 178448403HCID 178448403, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

5.0 g of 2,3-diaminopyridine in 200 g of polyphosphoric acid are heated at 120° C. for 0.5 h. The solution is cooled to 80° C. and 5.7 ml of 2-chlorobutyric acid are added. Thereafter, the reaction mixture is heated to 130° C. for 22 h. After cooling, the polyphosphoric acid is hydrolysed 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 three times each with 200 ml of ethyl acetate, the combined organic phases are dried using sodium sulfate, concentrated and the residue is purified by chromatography on silica gel (eluent: toluene/ethyl acetate 1:1) to give 5.19 g of the title compound as a colorless, amorpheous solid. M.p. 137° C. TLC: Rf=0.50 (dichloromethane/methanol 10:1).

Workup

  1. temperatureThereafter, the reaction mixture is heated to 130° C. for 22 h
  2. temperatureAfter cooling
  3. filtrationthe mixture is filtered
  4. extractionThe mixture is extracted three times each with 200 ml of ethyl acetate
  5. customthe combined organic phases are dried
  6. concentrationconcentrated
  7. customthe residue is purified by chromatography on silica gel (eluent: toluene/ethyl acetate 1:1)

Sources & evidence

ORD record
ord-accb37b4f26e4bf2999888ef5285ad22
Source dataset
uspto-grants-2008_02
Patent number
US07329677B2

Reaction notes

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