Hydrochloric Acid → Hydrochloric Acid

HRID 705401Notes

Reaction equation

HRID 705401 reaction equation
[C:1]([C:3]1[N:8]=[CH:7][C:6](C)=[C:5]([CH3:10])[CH:4]=1)#[N:2].[ClH:11].[H][H].[CH3:14]O>[Pd]>[NH2:2][CH2:1][C:3]1[C:4]([CH3:14])=[C:5]([CH3:10])[CH:6]=[CH:7][N:8]=1.[ClH:11]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 132444834,5-Dimethylpyridine-2-carbonitrileHCID 178418361HCID 178418361, compound

Product 2

HCID 313Hydrochloric AcidYield 93%HCID 18741291(3,4-Dimethylpyridin-2-YL)methylamine

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

In an autoclave, 3.40 g of 6-cyano-3,4-dimethylpyridine (25.7 mmol), 0.15 g of Pd/C (water-content=50%), 200 mL methanol and 3.0 mL concentrated hydrochloric acid are placed, stirred at room temperature for 3 hours while pressurizing with hydrogen to 3 atm. The reaction solution was filtered through Celite and the filtrate was concentrated to dryness. This was washed with methanol to give 2.41 g of 2-aminomethyl-3,4-dimethylpyridine (3,4-Me2PICA) hydrochloride (93% yield). This 2-aminomethyl-3,4-dimethylpyridine hydrochloride was treated with an aqueous solution of potassium carbonate to give 2-aminomethyl-3,4-dimethylpyridine (3,4-Me2PICA) quantitatively.

Workup

  1. filtrationThe reaction solution was filtered through Celite
  2. concentrationthe filtrate was concentrated to dryness
  3. washThis was washed with methanol

Sources & evidence

ORD record
ord-688ad2717a0a401bae18a55d74ade101
Source dataset
uspto-grants-2015_11
Patent number
US09174906B2

Reaction notes

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