4-Chloro-2-fluoroaniline → 4-(4-Chloro-2-fluoro-phenylamino)-6-fluoro-[1,7]naphthyridine-3-carbonitrile

HRID 276866Notes

Reaction equation

HRID 276866 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][N:8]=[C:9]([F:12])[CH:10]=2)[N:5]=[CH:4][C:3]=1[C:13]#[N:14].[Cl:15][C:16]1[CH:22]=[CH:21][C:19]([NH2:20])=[C:18]([F:23])[CH:17]=1.C(=O)(O)[O-].[Na+]>C(O)C.[Cl-].[Na+].O>[Cl:15][C:16]1[CH:22]=[CH:21][C:19]([NH:20][C:2]2[C:11]3[C:6](=[CH:7][N:8]=[C:9]([F:12])[CH:10]=3)[N:5]=[CH:4][C:3]=2[C:13]#[N:14])=[C:18]([F:23])[CH:17]=1

Participants

6

Reactant 3

HCID 938984-Chloro-2-fluoroanilineHCID 516892Sodium BicarbonateHCID 185489604-Chloro-6-fluoro-1,7-naphthyridine-3-carbonitrile

Product 1

HCID 185489394-(4-Chloro-2-fluoro-phenylamino)-6-fluoro-[1,7]naphthyridine-3-carbonitrile

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To 3.5 g of 4-chloro-6-fluoro-[1.7]naphthyridine-3-carbonitrile in 100 mL of absolute ethanol was added 2.3 mL of 4-chloro-2-fluoroaniline. After stirring the reaction under an inert atmosphere for 24 hours, the reaction mixture was poured into a mixture of brine and saturated aqueous sodium bicarbonate and the resultant crystals were filtered and washed with water. The product was then recrystallized from chloroform/ethyl acetate/hexanes. Drying in vacuo yielded 1.9 (40%) of 4-(4-chloro-2-fluoro-phenylamino)-6-fluoro-[1.7]naphthyridine-3-carbonitrile as yellow needles: melting point 249-252° C.; mass spectrum (m/e): M+H 316.9.

Workup

  1. customthe reaction under an inert atmosphere for 24 hours
  2. filtrationthe resultant crystals were filtered
  3. washwashed with water
  4. customThe product was then recrystallized from chloroform/ethyl acetate/hexanes
  5. customDrying in vacuo

Sources & evidence

ORD record
ord-14157c54cd7048f59f6f476b1bfa458e
Source dataset
uspto-grants-2002_03
Patent number
US06355636B1

Reaction notes

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