Hydrochloric Acid → 2-Aminomethyl-4,6-dimethoxy-1,3,5-triazine

HRID 2413077Notes

Reaction equation

HRID 2413077 reaction equation
[C:1]([C:3]1[N:8]=[C:7]([O:9][CH3:10])[N:6]=[C:5]([O:11][CH3:12])[N:4]=1)#[N:2].Cl>[Pd].CO>[NH2:2][CH2:1][C:3]1[N:4]=[C:5]([O:11][CH3:12])[N:6]=[C:7]([O:9][CH3:10])[N:8]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 23202681,3,5-Triazine-2-carbonitrile, 4,6-dimethoxy-

Product 1

HCID 133926782-Aminomethyl-4,6-dimethoxy-1,3,5-triazineYield 36.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 6.4 g of the product from Example 3, 0.69 g, 10% palladium-on-carbon catalyst, and 3 ml of concentrated hydrochloric acid in 140 ml methanol was shaken under an atmosphere of hydrogen at 50 p.s.i. on a Parr Hydrogenation Apparatus. After approximately 4 hours, the solution was filtered through a pad of Celite and the filtrate was concentrated in vacuo. The residue was diluted with water and, after being washed with several small portions of ether, the aqueous layer was made strongly basic to pH paper by the addition of 50% sodium hydroxide solution with ice-water cooling. A yellow solid precipitated from the basic solution and was isolated by filtration. Drying in vacuo for 24 hours gave 2.4 g of 2-aminomethyl-4,6-dimethoxy-1,3,5-triazine as a light yellow solid.

Workup

  1. filtrationthe solution was filtered through a pad of Celite
  2. concentrationthe filtrate was concentrated in vacuo
  3. additionThe residue was diluted with water
  4. washafter being washed with several small portions of ether
  5. additionby the addition of 50% sodium hydroxide solution with ice-water cooling
  6. customA yellow solid precipitated from the basic solution
  7. customwas isolated by filtration
  8. customDrying in vacuo for 24 hours

Sources & evidence

ORD record
ord-9ebc15e4bc5a4cf19328d401d37d44d7
Source dataset
uspto-grants-1985_01
Patent number
US04496392

Reaction notes

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