Toluene → 1-(5-Chloro-2-nitro-phenyl)-2,5-dimethyl-1H-pyrrole

HRID 646890Notes

Reaction equation

HRID 646890 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N+:9]([O-:11])=[O:10])=[C:6]([NH2:8])[CH:7]=1.[CH3:12][C:13](=O)[CH2:14][CH2:15][C:16](=O)[CH3:17].C1(C)C=CC=CC=1>C1COCC1.OS(O)(=O)=O.C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N+:9]([O-:11])=[O:10])=[C:6]([N:8]2[C:16]([CH3:17])=[CH:15][CH:14]=[C:13]2[CH3:12])[CH:7]=1

Participants

7

Reactant 3

HCID 1140TolueneHCID 80352,5-HexanedioneHCID 742185-Chloro-2-nitroaniline

Product 1

HCID 686806361-(5-Chloro-2-nitro-phenyl)-2,5-dimethyl-1H-pyrroleYield 25.3%

Reagents, catalysts & solvents 3

HCID 1118Sulfuric AcidCatalystHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
120 °C

Procedure

To a solution of 5-chloro-2-nitrophenylamine (200 mg, 1.15 mmol) and hexane-2,5-dione (326 μL, 2.78 mmol) in THF (3 mL) was added 1 drop of conc H2SO4. Toluene (3 mL) was then added and the reaction was allowed to stir at 120° C. overnight. At this time the reaction was diluted with CH2Cl2 (50 mL), washed with H2O (2×25 mL), dried (Na2SO4) and concentrated in vacuo. Purification by preparative thin layer chromatography (50% EtOAc-hexane) afforded 73 mg (25%) of the title compound as a tan solid. 1H-NMR (CDCl3; 400 MHz): δ 7.96 (d, 1H, J=8.7 Hz), 7.59-7.54 (m, 1H), 7.39 (d, 1H, J=2.0 Hz), 5.92 (s, 2H), 1.97 (s, 6H);

Workup

  1. washwashed with H2O (2×25 mL)
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated in vacuo
  4. customPurification by preparative thin layer chromatography (50% EtOAc-hexane)

Sources & evidence

ORD record
ord-7a17b172be4f430985f9a167cbd23c0a
Source dataset
uspto-grants-2010_04
Patent number
US07705042B2

Reaction notes

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