2-Nitroaniline → HCID 19744231, compound

HRID 2254111Notes

Reaction equation

HRID 2254111 reaction equation
[Cl: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.ClCl.C1(N)C=CC=CC=1N>C(OCC)(=O)C.C(O)(=O)C.C(Cl)(Cl)Cl.[Fe].O>[Cl: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 24526ChlorineHCID 19744228HCID 19744228, compound

Product 1

HCID 19744231HCID 19744231, compound

Reagents, catalysts & solvents 5

HCID 23925IronCatalystHCID 176Acetic AcidSolvent2×HCID 962WaterSolventHCID 6212ChloroformSolventHCID 8857Ethyl AcetateSolvent2×

Conditions

Temperature
50 °C

Procedure

5.6 Grams of 5-chloro-2-nitro-4-(1',1',2',2'-tetrafluoroethoxy)aniline [i.e. the o-nitroaniline compound (VI) containing chlorine as the substituent X] was dissolved in a mixed solvent of 25 ml of ethyl acetate and 25 ml of acetic acid. The resulting solution was dropwise added to a suspension of 4.7 g of iron powders in a mixed solution of 5 ml of acetic acid and 50 ml of water while maintaining the temperature at 50° C. Thereafter, stirring was continued for 20 minutes at 50° C. to 60° 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 and ethyl acetate as eluents to obtain 5.2 g of 4-chloro-5-(1',1',2',2'-tetrafluoroethoxy)-1,2-benzenediamine [i.e. the o-phenylenediamine compound (IV) containing chlorine as the substituent X]. 1H-NMR (CDCl3): δ(ppm) 6.65-6.75(2H), 5.95(1H, tt, J=53, 3 Hz), 3.40(4H, s, 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-08ea52f9efc947348b42d8c1bed6e76a
Source dataset
uspto-grants-1993_08
Patent number
US05234938

Reaction notes

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