Pyridine → HCID 66744359, compound

HRID 1396330Notes

Reaction equation

HRID 1396330 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 94%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Conditions

Temperature
0 °C

Procedure

To a solution of 4-iodo-3-nitroaniline (1.320 g, 5 mmol) in DCM (50 mL) and pyridine (0.445 mL, 5.50 mmol) at 0° C. was added methyl chloroformate (0.407 mL, 5.25 mmol) dropwise. After stirring at 0° C. for 3 h, HPLC analysis showed the reaction to be complete. The reaction was then diluted with DCM, washed with brine and dried over MgSO4 to yield the crude product. The crude product was then dissolved in minimal DCM (˜20 mL) and hexane (200 mL) was added to give a yellow suspension. Filtered the solid rinsing with hexane and air-dried the solids to obtain a yellow solid as the desired product (1.51 g, 94%). MS (ESI) m/z: 322.9 (M+H)+.

Workup

  1. customthe reaction
  2. washwashed with brine
  3. dry with materialdried over MgSO4
  4. customto yield the crude product
  5. customto give a yellow suspension
  6. filtrationFiltered the solid
  7. washrinsing with hexane
  8. customair-dried the solids

Sources & evidence

ORD record
ord-bf7501ddfd444f15a6f0d89b8bfd754c
Source dataset
uspto-grants-2014_12
Patent number
US08901115B2

Reaction notes

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