Isopropylamine → N-Isopropyl-2-nitroaniline

HRID 2250361Notes

Reaction equation

HRID 2250361 reaction equation
F[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N+:8]([O-:10])=[O:9].[CH:11]([NH2:14])([CH3:13])[CH3:12].C(=O)([O-])[O-].[K+].[K+]>C(O)C.O>[CH:11]([NH:14][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N+:8]([O-:10])=[O:9])([CH3:13])[CH3:12]

Participants

6

Reactant 3

HCID 6363IsopropylamineHCID 11430Potassium CarbonateHCID 738951-Fluoro-2-nitrobenzene

Product 1

HCID 10583518N-Isopropyl-2-nitroanilineYield 96.2%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

To a cold solution of 2-fluoro-nitrobenzene (31.8 g, 0.225 mol) in ethanol (300 mL) cooled in an ice bath was added isopropylamine (54.0 mL, 0.634 mol), followed by the addition of a solution of potassium carbonate (31.1 g, 0.225 mol) in water (120 mL). The mixture was stirred at 0° C. for 1 h, then refluxed for 6 h. The reaction was terminated by cooling the mixture to ambient temperature, and evaporating it under reduced pressure yielding an orange residue. The residue was partitioned between ethyl ether (800 mL) and a brine solution (300 mL). The organic layer was dried and filtered, to provide the title intermediate (39 g) as an orange liquid. 1H-NMR (CDCl3, 300 MHz): δ (ppm) 8.06 (d, 1H), 7.30 (t, 1H), 6.74 (d, 1H), 6.48 (t, 1H), 3.73 (hept, 1H), 1.20 (d, 6H).

Workup

  1. temperaturerefluxed for 6 h
  2. customThe reaction was terminated
  3. temperatureby cooling the mixture to ambient temperature
  4. customevaporating it under reduced pressure
  5. customyielding an orange residue
  6. customThe residue was partitioned between ethyl ether (800 mL)
  7. customThe organic layer was dried
  8. filtrationfiltered

Sources & evidence

ORD record
ord-931f6c4a17b042fea7be0bd7b0eb48a2
Source dataset
uspto-grants-2008_01
Patent number
US07317022B2

Reaction notes

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