Acetic Acid → HCID 67406226, compound

HRID 1867293Notes

Reaction equation

HRID 1867293 reaction equation
C(O)(=O)C.[Cl:5][C:6]1[CH:11]=[C:10]([N+:12]([O-])=O)[CH:9]=[C:8]([C:15]([F:18])([F:17])[F:16])[C:7]=1[NH2:19]>O1CCCC1.[Zn]>[Cl:5][C:6]1[CH:11]=[C:10]([NH2:12])[CH:9]=[C:8]([C:15]([F:18])([F:17])[F:16])[C:7]=1[NH2:19]

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 137844272-Chloro-4-nitro-6-(trifluoromethyl)aniline

Product 1

HCID 67406226HCID 67406226, compoundYield 83%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 8028TetrahydrofuranSolvent

Procedure

Acetic acid (13 mL) was added slowly to a mixture of zinc dust (12.4 g) and 2-chloro-4-nitro-6-trifluoromethyl-phenylamine (4 g) in tetrahydrofuran (40 mL). The reaction mixture was stirred for 1 hour, filtered through silica and concentrated in vacuo. The crude product was purified by flash chromatography to furnish 2.9 g (83%) of the title compound as a black solid. 1H NMR (500 MHz, CDCl3): 3.44 (b, 2H), 4.16 (b, 2H), 6.77 (d, 1H), 6.86 (d, 1H).

Workup

  1. filtrationfiltered through silica
  2. concentrationconcentrated in vacuo
  3. customThe crude product was purified by flash chromatography

Sources & evidence

ORD record
ord-e5b8e8456ad8469893cdca1b1f91d7f4
Source dataset
uspto-grants-2009_12
Patent number
US07632835B2

Reaction notes

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