Acetic Acid → 3-Fluoropicolinimidamide hydrochloride

HRID 2109422Notes

Reaction equation

HRID 2109422 reaction equation
[C:1]([C:3]1[C:8]([F:9])=[CH:7][CH:6]=[CH:5][N:4]=1)#[N:2].[Na].[Cl-:11].[NH4+:12].C(O)(=O)C>CO>[ClH:11].[C:1]([C:3]1[C:8]([F:9])=[CH:7][CH:6]=[CH:5][N:4]=1)(=[NH:12])[NH2:2]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 25517Ammonium ChlorideHCID 5360545SodiumHCID 70604082-Cyano-3-fluoropyridine

Product 1

HCID 220278373-Fluoropicolinimidamide hydrochloride

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Conditions

Temperature
20 °C

Procedure

10.30 g (84.355 mmol) of the compound from Example II are dissolved in 30 ml of methanol. The solution is admixed with a solution of 0.40 g (17.391 mmol) of sodium in 65 ml of methanol and stirred at 20° C. for 72 hours. 5.44 g (101.682 mmol) of ammonium chloride (ground in a mortar) and 17.39 mmol (1.04 ml) of acetic acid are added and the mixture is stirred at 40° C. for 28 hours and cooled. Insoluble salt is filtered off with suction (1.78 g) and the filtrate is concentrated, concentrated with acetone and subsequently stirred with acetone, filtered off with suction and washed.

Workup

  1. stirringthe mixture is stirred at 40° C. for 28 hours
  2. temperaturecooled
  3. filtrationInsoluble salt is filtered off with suction (1.78 g)
  4. concentrationthe filtrate is concentrated
  5. concentrationconcentrated with acetone
  6. stirringsubsequently stirred with acetone
  7. filtrationfiltered off with suction
  8. washwashed

Sources & evidence

ORD record
ord-eb6728a3065c435a83192c0dd65b930e
Source dataset
uspto-grants-2009_04
Patent number
US07514565B2

Reaction notes

Loading…