2-Nitroaniline → HCID 19744226, compound

HRID 2254110Notes

Reaction equation

HRID 2254110 reaction equation
[F:1][C:2]1[C:3]([O:12][C:13]([F:18])([F:17])[CH:14]([F:16])[F:15])=[CH:4][C:5]([N+:9]([O-])=O)=[C:6]([CH:8]=1)[NH2:7].[N+](C1C=CC=CC=1N)([O-])=O.FF.C1(N)C=CC=CC=1N>C(OCC)(=O)C.C(O)(=O)C.C(Cl)(Cl)Cl.[Fe].O>[F:1][C:2]1[CH:8]=[C:6]([NH2:7])[C:5]([NH2:9])=[CH:4][C:3]=1[O:12][C:13]([F:18])([F:17])[CH:14]([F:15])[F:16]

Participants

10

Reactant 4

HCID 69462-NitroanilineHCID 7243O-PhenylenediamineHCID 24524FluorineHCID 19744227HCID 19744227, compound

Product 1

HCID 19744226HCID 19744226, compound

Reagents, catalysts & solvents 5

HCID 23925IronCatalystHCID 176Acetic AcidSolvent2×HCID 962WaterSolventHCID 6212ChloroformSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
40 °C

Procedure

4.7 Grams of 5-fluoro-2-nitro-4-(1',1',2',2'-tetrafluoroethoxy)aniline [i.e. the o-nitroaniline compound (VI) containing fluorine as the substituent X] was dissolved in a mixed solvent of 15 ml of ethyl acetate and 15 ml of acetic acid. The resulting solution was dropwise added to a suspension of 4.8 g of iron powders in a mixed solution of 3 ml of acetic acid and 30 ml of water while maintaining the temperature at 40° C. Thereafter, stirring was continued for 15 minutes at 40° C. to 50° C. The reaction solution was filtered through Celite, and the filtrate was extracted with ethyl acetate. The organic layer was washed with an aqueous sodium hydrogencarbonate solution and water in this order, dried over anhydrous magnesium sulfate and concentrated. The residue obtained was subjected to column chromatography on silica gel with chloroform as an eluent to obtain 3.9 g of 4-fluoro-5-(1',1',2',2'-tetrafluoroethoxy)-1,2-benzenediamine [i.e. the o-phenylenediamine compound (IV) containing fluorine as the substituent X]. 1H-NMR (CDCl3): δppm 6.40-6.70(2H), 5.90(1H, tt, J=54, 3 Hz), 3.30(4H, broad).

Workup

  1. filtrationThe reaction solution was filtered through Celite
  2. extractionthe filtrate was extracted with ethyl acetate
  3. washThe organic layer was washed with an aqueous sodium hydrogencarbonate solution and water in this order
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated
  6. customThe residue obtained

Sources & evidence

ORD record
ord-e30d3eaf3df2437b83560c7a515463cf
Source dataset
uspto-grants-1993_08
Patent number
US05234938

Reaction notes

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