Propylamine → HCID 178457528, compound

HRID 1607086Notes

Reaction equation

HRID 1607086 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([NH:8][CH:9]=[N:10][C:11]#N)[N:3]=1.[CH2:13](N)[CH2:14]C>O>[OH:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([NH:8][CH:9]=[N:10][CH2:11][CH2:13][CH3:14])[N:3]=1

Participants

4

Reactant 2

HCID 7852PropylamineHCID 178512261HCID 178512261, compound

Product 1

HCID 178457528HCID 178457528, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2.3 g (14 mmol) of N-(2-hydroxy-6-pyridyl)-N'-cyanoformamidine are added in portions at room temperature over a period of 20 minutes to a stirred solution of 8.3 ml (99 mmol) of n-propylamine in 8 ml of water The reaction mixture is stirred for 2 hours at room temperature It is then extracted three times with chloroform The combined organic phases are dried over MgSO4 and concentrated by evaporation. The resulting crude product is chromatographed on silica gel with methylene chloride and then crystallised from ether/n-hexane. N-(2-pyridon-6-yl)-N'-propylformamidine and N-(2-hydroxy-6-pyridyl)-N'-propylformamidine having a melting point of 178°-179° are obtained.

Workup

  1. extractionis then extracted three times with chloroform The combined organic phases
  2. dry with materialare dried over MgSO4
  3. concentrationconcentrated by evaporation
  4. customThe resulting crude product is chromatographed on silica gel with methylene chloride
  5. customcrystallised from ether/n-hexane

Sources & evidence

ORD record
ord-aad0c63e0b1e42f486e5574c2ef82aa0
Source dataset
uspto-grants-1989_09
Patent number
US04863938

Reaction notes

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