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

HRID 2088856Notes

Reaction equation

HRID 2088856 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([NH:8][CH2:9][CH3:10])[C:5]([C:11]([OH:13])=O)=[CH:4][CH:3]=1.N1C=CC=CC=1.N1C(F)=NC(F)=NC=1[F:22]>ClCCl>[Cl:1][C:2]1[N:7]=[C:6]([NH:8][CH2:9][CH3:10])[C:5]([C:11]([F:22])=[O:13])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 12664Cyanuric fluorideHCID 633764796-Chloro-2-(ethylamino)nicotinic acid

Product 1

HCID 867145746-Chloro-2-(ethylamino)pyridine-3-carbonyl fluorideYield 99%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of 10.5 g (52.3 mmol) of the compound obtained in step 1.1 in dichloromethane (250 ml) are successively added 4.2 ml (52.3 mmol) of pyridine and 8.4 ml (99.6 mmol) of cyanuric fluoride. The mixture is stirred for 3 hours at room temperature and then filtered. The solid is rinsed with dichloromethane (100 ml) and the filtrate is washed twice with ice-cold water (60 ml). The organic phase is dried over Na2SO4 and then concentrated under reduced pressure. 10.44 g of product are obtained, the form of an orange-coloured oil. Yield=99%. The product is used without purification in the following step.

Workup

  1. filtrationfiltered
  2. washThe solid is rinsed with dichloromethane (100 ml)
  3. washthe filtrate is washed twice with ice-cold water (60 ml)
  4. dry with materialThe organic phase is dried over Na2SO4
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-3e6fcac51b144091a84abeee34028be9
Source dataset
uspto-grants-2013_05
Patent number
US08436011B2

Reaction notes

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