HCID 10542584, compound → 3-Chloro-2,4-difluoro-6-nitroaniline

HRID 1780996Notes

Reaction equation

HRID 1780996 reaction equation
[Cl:1][C:2]1[C:3]([F:19])=[C:4]([NH:12]C(=O)C(F)(F)F)[C:5]([N+:9]([O-:11])=[O:10])=[CH:6][C:7]=1[F:8]>C([O-])([O-])=O.[K+].[K+].CO.O>[Cl:1][C:2]1[C:3]([F:19])=[C:4]([C:5]([N+:9]([O-:11])=[O:10])=[CH:6][C:7]=1[F:8])[NH2:12]

Participants

3

Reactant 1

HCID 10542584HCID 10542584, compound

Product 1

HCID 106560013-Chloro-2,4-difluoro-6-nitroanilineYield 6.9%

Reagents, catalysts & solvents 1

HCID 86616699K2CO3 methanol waterSolvent

Procedure

A solution of 6.35 g (20.8 mmol) of 3-chloro-2,4-difluoro-6-nitro-(trifluoroacetamido)benzene in 60 mL of 7% K2CO3 methanol/water (3:2) was stirred at 25° C. for 4 h. The solution was evaporated to remove the methanol. Solid was observed in the residue. It was filtered, washed with water, and dried to leave 301 mg of a crystalline yellow solid; mp 96°-97° C.; 1H NMR (CDCl3), 6.07 (mb, 2), 7.815 (dd, 1, J=1.92, 9.13). More solid was observed after the mother aqueous solution was allowed to stand at room temperature overnight. It was filtered, washed with water, and dried to leave a yellow solid (1.01 g). More solid was crystallized from the mother solution. It was collected three more times to provide 2.48 g of a yellow solid. 1H NMR is identical with above, total yield 3.80 g (87%).

Workup

  1. customThe solution was evaporated
  2. customto remove the methanol
  3. filtrationIt was filtered
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-c0b2172acf044bee8060c3836fd1650a
Source dataset
uspto-grants-1997_05
Patent number
US05631373

Reaction notes

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