Sodium Chloride → N-tert-Butyl-2-nitroaniline

HRID 2110383Notes

Reaction equation

HRID 2110383 reaction equation
F[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N+:8]([O-:10])=[O:9].[C:11]([NH2:15])([CH3:14])([CH3:13])[CH3:12].[Cl-].[Na+]>CN(C)C=O>[C:11]([NH:15][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N+:8]([O-:10])=[O:9])([CH3:14])([CH3:13])[CH3:12]

Participants

5

Reactant 3

HCID 5234Sodium ChlorideHCID 6385Tert-ButylamineHCID 738951-Fluoro-2-nitrobenzene

Product 1

HCID 10797892N-tert-Butyl-2-nitroaniline

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 1-fluoro-2-nitro-benzene (1 g, 7.1 mmol) in dimethylformamide (15 mL) was added tert-butyl amine (0.82 mL, 7.81 mmol) at room temperature, and the reaction mixture stirred for 12 hours at room temperature under nitrogen. Upon completion, the reaction mixture was poured into a saturated aqueous solution of sodium chloride (50 mL) and extracted with ethyl acetate (50 mL). The organic layer was dried over anhydrous sodium sulfate, concentrated in vacuo, and the residue was purified via flash column chromatography (silica, 1% ethyl acetate in hexane) to give tert-butyl-(2-nitrophenyl)-amine as an orange oil. MS (ES) m/z 195.2

Workup

  1. extractionextracted with ethyl acetate (50 mL)
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. concentrationconcentrated in vacuo
  4. customthe residue was purified via flash column chromatography (silica, 1% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-203045e470a64bd19e18d29810cf970e
Source dataset
uspto-grants-2009_04
Patent number
US07517899B2

Reaction notes

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