Ammonium Chloride → HCID 18365067, compound

HRID 380393Notes

Reaction equation

HRID 380393 reaction equation
[C:1]([C:4]1[CH:5]=[N:6][CH:7]=[CH:8][C:9]=1[NH2:10])(=[NH:3])[NH2:2].[Cl-:11].[NH4+].C[Al](C)C.NC1C=CN=CC=1C#N>C1(C)C=CC=CC=1.C(Cl)(Cl)Cl>[ClH:11].[C:1]([C:4]1[CH:5]=[N:6][CH:7]=[CH:8][C:9]=1[NH2:10])(=[NH:2])[NH2:3]

Participants

7

Reactant 4

HCID 25517Ammonium ChlorideHCID 5770164-Amino-nicotinonitrileHCID 16682925TrimethylaluminumHCID 18365068HCID 18365068, compound

Product 1

HCID 18365067HCID 18365067, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6212ChloroformSolvent

Procedure

3-Amidino-4-aminopyridine To ammonium chloride (430 mg, 8.1 mmol) in toluene was added trimethylaluminium (2M in hexane, 4 ml, 8.1 mmol) at 5° C. and the mixture was stirred at room temperature for 2 h. 4-Amino-3-cyanopyridine (320 mg, 2.7 mmol) was added and the reaction mixture was heated at 80° C. overnight. The mixture was cooled, poured onto alumina in chloroform, quenched with ethanol and filtered. The filtrate was concentrated and triturated with ether to give a solid. MS (+EI) m/z 119 (M−NH3)+.

Workup

  1. temperaturethe reaction mixture was heated at 80° C. overnight
  2. temperatureThe mixture was cooled
  3. customquenched with ethanol
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated
  6. customtriturated with ether
  7. customto give a solid

Sources & evidence

ORD record
ord-c8d9879740d942b6bf47aa124a492fc5
Source dataset
uspto-grants-2001_10
Patent number
US06303613B1

Reaction notes

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