2,4-Dichloroaniline → HCID 18548948, compound

HRID 276864Notes

Reaction equation

HRID 276864 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]=[C:21]([Cl:23])[CH:20]=[CH:19][C:17]=1[NH2:18].C(=O)(O)[O-].[Na+]>CO.[Cl-].[Na+].O>[Cl:15][C:16]1[CH:22]=[C:21]([Cl:23])[CH:20]=[CH:19][C:17]=1[NH:18][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]

Participants

6

Reactant 3

HCID 111232,4-DichloroanilineHCID 516892Sodium BicarbonateHCID 185489604-Chloro-6-fluoro-1,7-naphthyridine-3-carbonitrile

Product 1

HCID 18548948HCID 18548948, compoundYield 81%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To 2.0 g of 4-chloro-6-fluoro-[1.7]naphthyridine-3-carbonitrile in 50 mL of methanol was added 1.9 g of 2,4-dichloroaniline. After refluxing the reaction under an inert atmosphere for 2 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/hexanes. Drying in vacuo yielded 2.6 g (80%) of 4-(2,4-dichloro-phenylamino)-6-fluoro-[1.7]naphthyridine-3-carbonitrile as yellow needles: melting point 206-208° C.; mass spectrum (m/e): M+H 332.8.

Workup

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

Sources & evidence

ORD record
ord-f4bf3e05b2104395a2df6637f6f3896f
Source dataset
uspto-grants-2002_03
Patent number
US06355636B1

Reaction notes

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