4-Chloro-2-nitroaniline → 1-(2-Nitro-4-chlorophenoxy)-2,2,6,6-tetramethylpiperidine

HRID 1369341Notes

Reaction equation

HRID 1369341 reaction equation
[OH:1][N:2]1[C:7]([CH3:9])([CH3:8])[CH2:6][CH2:5][CH2:4][C:3]1([CH3:11])[CH3:10].N(OC(C)(C)C)=O.[N+:19]([C:22]1[CH:28]=[C:27]([Cl:29])[CH:26]=[CH:25][C:23]=1N)([O-:21])=[O:20]>[Cu](F)F.N1C=CC=CC=1>[N+:19]([C:22]1[CH:28]=[C:27]([Cl:29])[CH:26]=[CH:25][C:23]=1[O:1][N:2]1[C:7]([CH3:9])([CH3:8])[CH2:6][CH2:5][CH2:4][C:3]1([CH3:11])[CH3:10])([O-:21])=[O:20]

Participants

6

Reactant 3

HCID 69794-Chloro-2-nitroanilineHCID 10906Tert-Butyl nitriteHCID 5499762,2,6,6-Tetramethylpiperidin-1-ol

Product 1

HCID 120843001-(2-Nitro-4-chlorophenoxy)-2,2,6,6-tetramethylpiperidineYield 66.7%

Reagents, catalysts & solvents 2

HCID 522688Copper fluorideCatalystHCID 1049PyridineSolvent

Procedure

The procedure of Example 1 is repeated using 3.9 g (25 mmol) of 1-oxyl-2,2,6,6-tetramethylpiperidine, 7.84 g (76 mmol) of tert-butyl nitrite, 25 mg (0.25 mmol) of copper(II) fluoride, 120 mL of pyridine and 8.6 g (50 mmol) of 2-nitro-4-chloroaniline at 70° C. The crude product obtained is purified by vacuum flash chromatography (heptane) to give 5.2 g of the title compound as a light yellow oil in 66.7% yield. The structure is confirmed by 1Hnmr and mass spectroscopy analyses.

Workup

  1. customat 70° C
  2. customThe crude product obtained
  3. customis purified by vacuum flash chromatography (heptane)

Sources & evidence

ORD record
ord-212b3b41392041bdbd372c39b3a96d7a
Source dataset
uspto-grants-2003_06
Patent number
US06579328B2

Reaction notes

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