Pyridine → 2-(Aminoethyl)-6-chloronicotinic acid fluoride

HRID 1260573Notes

Reaction equation

HRID 1260573 reaction equation
N1C=CC=CC=1.[F:7]N1N=C(F)C=C(F)N1.[NH2:16][CH2:17][CH2:18][C:19]1[N:27]=[C:26]([Cl:28])[CH:25]=[CH:24][C:20]=1[C:21](O)=[O:22]>ClCCl>[NH2:16][CH2:17][CH2:18][C:19]1[N:27]=[C:26]([Cl:28])[CH:25]=[CH:24][C:20]=1[C:21]([F:7])=[O:22]

Participants

5

Reactant 3

HCID 1049PyridineHCID 216944332,4,6-Trifluoro-1,2,3-triazineHCID 866423332-(Aminoethyl)-6-chloronicotinic acid

Product 1

HCID 874003732-(Aminoethyl)-6-chloronicotinic acid 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-(aminoethyl)-6-chloronicotinic acid in 125 ml of dichloromethane. The mixture is stirred for 3 hours at ambient temperature 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 off 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 off under reduced pressure

Sources & evidence

ORD record
ord-e0b571ab32624b038919e26a9dcf91a4
Source dataset
uspto-grants-2013_06
Patent number
US08470847B2

Reaction notes

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