Hydrochloric Acid → (2-Isopropylpyridin-4-yl)methanamine

HRID 2070926Notes

Reaction equation

HRID 2070926 reaction equation
[CH2:1]=[C:2]([C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][N:11]=1)[C:7]#[N:8])[CH3:3].Cl>CO.[Pd]>[CH:2]([C:4]1[CH:5]=[C:6]([CH2:7][NH2:8])[CH:9]=[CH:10][N:11]=1)([CH3:3])[CH3:1]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 686710942-(Prop-1-en-2-yl)isonicotinonitrile

Product 1

HCID 59569820(2-Isopropylpyridin-4-yl)methanamineYield 59.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 154 mg (1.07 mmol) of 2-(prop-1-en-2-yl)isonicotinonitrile and 19.2 mg of 10% Pd/C with 1.7 mL of 1.25 N HCl in 10 mL of MeOH was stirred at r.t. under H2 balloon for 14 h. The mixture was filtered through Celite and concentrated. Saturated NaHCO3 was added, and the mixture concentrated with methanol, filtered through a sintered funnel, and reconcentrated to give 95.1 mg of crude (2-isopropylpyridin-4-yl)methanamine which was used without further purification.

Workup

  1. filtrationThe mixture was filtered through Celite
  2. concentrationconcentrated
  3. additionSaturated NaHCO3 was added
  4. concentrationthe mixture concentrated with methanol
  5. filtrationfiltered through a sintered funnel

Sources & evidence

ORD record
ord-5ddce74ee6ef4ba18208a2bbbfd5cdec
Source dataset
uspto-grants-2012_10
Patent number
US08299267B2

Reaction notes

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