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

HRID 53797Notes

Reaction equation

HRID 53797 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 and it was filtered and washed by water, and dried to leave 301 mg of 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 and washed by water, and dried to leave yellow solid (1.01 g). More solid was crystallized from the mother solution. It was collected three more times to leave 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. filtrationwas filtered
  4. washwashed by water
  5. customdried

Sources & evidence

ORD record
ord-1ad50d50e4b44881a650ffe10f150f23
Source dataset
uspto-grants-1997_04
Patent number
US05620979

Reaction notes

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