Pyridine → HCID 66744359, compound

HRID 1396313Notes

Reaction equation

HRID 1396313 reaction equation
[I:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10].N1C=CC=CC=1.Cl[C:19]([O:21][CH3:22])=[O:20].CCCCCC>C(Cl)Cl>[I:1][C:2]1[CH:8]=[CH:7][C:5]([NH:6][C:19](=[O:20])[O:21][CH3:22])=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10]

Participants

6

Reactant 4

HCID 1049PyridineHCID 6586Methyl chloroformateHCID 8058HexaneHCID 2849504-Iodo-3-nitroaniline

Product 1

HCID 66744359HCID 66744359, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

To a cooled (0° C.), yellow suspension of 4-iodo-3-nitroaniline (8.46 g, 32.0 mmol) in DCM (320 mL) and pyridine (2.85 mL, 35.2 mmol) was added methyl chloroformate (2.61 mL, 33.6 mmol) dropwise. The reaction mixture turned to light yellow solution and stirring was continued for 1.5 h. After 1.5 h, the reaction mixture was diluted with DCM, washed with saturated NaHCO3 solution followed by brine. The organic layers were dried over MgSO4, filtered and concentrated to obtain a residue. The residue was then dissolved in DCM (˜100 mL), then hexane (600 mL) was added to give a yellow suspension. The above suspension was filtered and the filtered solid was rinsed with hexane and air-dried to obtain the desired product as yellow solid (10.3 g, 100%). MS (ESI) m/z: 321.3 (M−H)+.

Workup

  1. temperatureTo a cooled
  2. waitAfter 1.5 h
  3. washwashed with saturated NaHCO3 solution
  4. dry with materialThe organic layers were dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto obtain a residue
  8. customto give a yellow suspension
  9. filtrationThe above suspension was filtered
  10. washthe filtered solid was rinsed with hexane
  11. customair-dried

Sources & evidence

ORD record
ord-1adb6ddf278947a687db273702d97c19
Source dataset
uspto-grants-2014_12
Patent number
US08901115B2

Reaction notes

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