Sodium Sulfate → HCID 14028992, compound

HRID 1651282Notes

Reaction equation

HRID 1651282 reaction equation
S([O-])([O-])(=O)=O.[Na+].[Na+].[C:8]([C:10]1[C:11]([F:24])=[N:12][C:13]2[C:18]([C:19]=1[F:20])=[CH:17][C:16]([N+:21]([O-])=O)=[CH:15][CH:14]=2)#[N:9].[H][H]>[Pd].O1CCCC1>[NH2:21][C:16]1[CH:17]=[C:18]2[C:13](=[CH:14][CH:15]=1)[N:12]=[C:11]([F:24])[C:10]([C:8]#[N:9])=[C:19]2[F:20]

Participants

6

Reactant 3

HCID 24436Sodium SulfateHCID 140289912,4-Difluoro-6-nitro-3-quinolinecarbonitrileHCID 178418361HCID 178418361, compound

Product 1

HCID 14028992HCID 14028992, compoundYield 74%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

130 parts of anhydrous sodium sulfate were suspended in a solution of 305 parts of 3-cyano-2,4-difluoro-6-nitro-quinoline in 3,400 parts of tetrahydrofuran. 30 parts of a hydrogenation catalyst (10% palladium on carbon) were added, which was followed by hydrogenation at 40° C. and 3 bar. After the uptake of hydrogen had ended, the suspension was filtered, and the clear solution was added to 6,000 parts of ice-water. The resulting precipitate was filtered off with suction, washed and dried. This gave 198 parts of 6-amino-3-cyano-2,4-difluoroquinoline, corresponding to a yield of 74%.

Workup

  1. customwas followed by hydrogenation at 40° C.
  2. filtrationthe suspension was filtered
  3. additionthe clear solution was added to 6,000 parts of ice-water
  4. filtrationThe resulting precipitate was filtered off with suction
  5. washwashed
  6. customdried

Sources & evidence

ORD record
ord-24a0b9103b5c45ada761f4e673c5645c
Source dataset
uspto-grants-1990_05
Patent number
US04927935

Reaction notes

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