Pyridine → 6-Chloro-2-(ethylamino)pyridine-3-carbonyl fluoride

HRID 2383232Notes

Reaction equation

HRID 2383232 reaction equation
N1C=CC=CC=1.[F:7]N1N=C(F)C=C(F)N1.[CH2:16]([NH:18][C:19]1[N:27]=[C:26]([Cl:28])[CH:25]=[CH:24][C:20]=1[C:21](O)=[O:22])[CH3:17]>ClCCl>[CH2:16]([NH:18][C:19]1[N:27]=[C:26]([Cl:28])[CH:25]=[CH:24][C:20]=1[C:21]([F:7])=[O:22])[CH3:17]

Participants

5

Reactant 3

HCID 1049PyridineHCID 216944332,4,6-Trifluoro-1,2,3-triazineHCID 633764796-Chloro-2-(ethylamino)nicotinic acid

Product 1

HCID 867145746-Chloro-2-(ethylamino)pyridine-3-carbonyl fluorideYield 99.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2 ml (24.8 mmol) of pyridine and 4.2 ml (49.8 mmol) of 2,4,6-trifluorotriazine are added to a suspension of 5.0 g (24.8 mmol) of 2-(ethylamino)-6-chloronicotinic acid in 125 ml of dichloromethane. The mixture is stirred at ambient temperature for 3 hours and then filtered. The solid is rinsed with 50 ml of dichloromethane and the filtrate is washed twice with 60 ml of ice-cold water. The organic phase is dried over Na2SO4 and the solvent is evaporated under reduced pressure. 5.01 g of product are obtained in the form of an orange oil. Yield=99%.

Workup

  1. filtrationfiltered
  2. washThe solid is rinsed with 50 ml of dichloromethane
  3. washthe filtrate is washed twice with 60 ml of ice-cold water
  4. dry with materialThe organic phase is dried over Na2SO4
  5. customthe solvent is evaporated under reduced pressure

Sources & evidence

ORD record
ord-c110c70f329045f189c452c73f4b2f85
Source dataset
uspto-grants-2012_09
Patent number
US08263614B2

Reaction notes

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