HCID 22493769, compound → HCID 22493781, compound

HRID 1816419Notes

Reaction equation

HRID 1816419 reaction equation
[NH2:1][CH:2]([CH3:13])[CH2:3][C:4]1[C:9]([N+:10]([O-])=O)=[CH:8][CH:7]=[CH:6][N:5]=1>C(OCC)(=O)C.C(O)C>[NH2:1][CH:2]([CH3:13])[CH2:3][C:4]1[C:9]([NH2:10])=[CH:8][CH:7]=[CH:6][N:5]=1

Participants

3

Reactant 1

HCID 22493769HCID 22493769, compound

Product 1

HCID 22493781HCID 22493781, compoundYield 100.1%

Reagents, catalysts & solvents 1

HCID 21584252Ethanol ethylacetateSolvent

Procedure

2-aminopropyl-3-nitropyridine (171) (6.3 g, 35 mmol) is dissolved in 100 mL 1/1 ethyl acetate/ethanol in a Parr shaker bottle. Nitrogen is bubbled through the solution for 2 minutes followed by the addition of 10% Pd/C (500 mg). The suspension is hydrogenated on a Parr apparatus under 40 psi of H2 until hydrogen uptake ceased. The suspension is filtered through Celite and the solvent evaporated in vacuo to afford 5.3 g of the 2-aminopropyl-3-aminopyridine (182). 1-propyl-2-chloromethyl-7-azabenzsmidazole

Workup

  1. customNitrogen is bubbled through the solution for 2 minutes
  2. additionfollowed by the addition of 10% Pd/C (500 mg)
  3. filtrationThe suspension is filtered through Celite
  4. customthe solvent evaporated in vacuo

Sources & evidence

ORD record
ord-b5b3b10018df4ace8226d4e36e27e4b0
Source dataset
uspto-grants-2005_04
Patent number
US06884815B1

Reaction notes

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