2-Pyridinemethanamine → HCID 178512370, compound

HRID 247373Notes

Reaction equation

HRID 247373 reaction equation
[NH2:1][CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][N:4]=1.[C:9]([NH:11][C:12](=[NH:21])OC1C=C(C)C=CC=1)#[N:10]>C(O)(C)C>[C:9]([NH:11][C:12]([NH:1][CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][N:4]=1)=[NH:21])#[N:10]

Participants

4

Reactant 2

HCID 195092-PyridinemethanamineHCID 178425733HCID 178425733, compound

Product 1

HCID 178512370HCID 178512370, compoundYield 40.4%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A mixture of 2-amino methyl pyridine (10.91 g) and 1-cyano-2-(3-tolyl)pseudourea (17.52 g) in 250 ml of isopropanol is stirred at reflux under a nitrogen atmosphere for 5 hours. The reaction mixture is allowed to cool to room temperature and the solvent is removed in vacuo. The dark green residual oil is stirred in 250 ml of diethyl ether. The resultant solid is collected and washed with ether, and ground to a paste in 100 ml of diethyl ether. The solid is filtered, washed with ether and dried in air. The solid is taken up in boiling acetone and filtered hot, concentrated in a hot plate and cooled. The precipitate is collected and recrystallized from acetone to yield 7.08 g of the cyano guanidine, MP 144° C.

Workup

  1. temperatureat reflux under a nitrogen atmosphere for 5 hours
  2. customthe solvent is removed in vacuo
  3. stirringThe dark green residual oil is stirred in 250 ml of diethyl ether
  4. customThe resultant solid is collected
  5. washwashed with ether, and ground to a paste in 100 ml of diethyl ether
  6. filtrationThe solid is filtered
  7. washwashed with ether
  8. customdried in air
  9. filtrationfiltered hot
  10. concentrationconcentrated in a hot plate
  11. temperaturecooled
  12. customThe precipitate is collected
  13. customrecrystallized from acetone

Sources & evidence

ORD record
ord-86aa6cd2ff844e769be74dcaa40ed754
Source dataset
uspto-grants-1987_11
Patent number
US04707478

Reaction notes

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