Acetic Acid → 3-Fluoropicolinimidamide hydrochloride

HRID 1791117Notes

Reaction equation

HRID 1791117 reaction equation
C[O-].[Na+].[Na].[C:5]([C:7]1[C:12]([F:13])=[CH:11][CH:10]=[CH:9][N:8]=1)#[N:6].[Cl-:14].[NH4+:15].C(O)(=O)C>CO>[ClH:14].[C:5]([C:7]1[C:12]([F:13])=[CH:11][CH:10]=[CH:9][N:8]=1)(=[NH:15])[NH2:6]

Participants

7

Reactant 5

HCID 176Acetic AcidHCID 25517Ammonium ChlorideHCID 5360545SodiumHCID 70604082-Cyano-3-fluoropyridineHCID 10942334Sodium Methoxide

Product 1

HCID 220278373-Fluoropicolinimidamide hydrochloride

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Conditions

Temperature
20 °C

Procedure

A sodium methoxide solution made from 0.40 g (17.391 mmol) of sodium and 65 ml of methanol is added to a solution of 10.30 g (84.355 mmol) of the compound from Example II in 30 ml of methanol, and the mixture is stirred at 20° C. for 72 hours. 5.44 g (101.682 mmol) of ammonium chloride (powdered) 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 then 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. stirringstirred with acetone
  7. filtrationfiltered off with suction
  8. washwashed

Sources & evidence

ORD record
ord-215e1a78f78e40ffbc1ff706fef971b2
Source dataset
uspto-grants-2006_07
Patent number
US07074784B2

Reaction notes

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