Toluene → HCID 19047729, compound

HRID 1780818Notes

Reaction equation

HRID 1780818 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:11]=[CH:12][C:13]=1Cl)[C:7]([O:9][CH3:10])=[O:8])([O-:3])=[O:2].N12[CH2:25][CH2:24]CN=C1CCCCC2.[N+](CC)([O-])=[O:27].C1(C)C=CC=CC=1>C(OCC)(=O)C>[C:24]([C:13]1[CH:12]=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[CH:5][C:4]=1[N+:1]([O-:3])=[O:2])(=[O:27])[CH3:25]

Participants

6

Reactant 4

HCID 1140TolueneHCID 6587NitroethaneHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 735797Methyl 4-chloro-3-nitrobenzoate

Product 1

HCID 19047729HCID 19047729, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A solution of methyl 3-nitro-4-chlorobenzoate (0.70 g) in ethyl acetate (2 mL) was added to a solution of 1,8-diazabicyclo[5.4.0]undec-7-ene (1.50 mL) and nitroethane (0.70 mL) at 0° C. The mixture was stirred for 5 h and partitioned with ethyl acetate and water. Potassium permanganate (0.57 g) was added to the water layer and resulting solution was stirred for 45 minutes. Toluene (20 mL) was added and mixture was stirred slowly. The toluene layer was separated and washed with saturated sodium chloride, dried over magnesium sulfate and concentrated in vacuo to afford the crude product. Purification on silica gel with hexane/ethyl acetate 7/3 gave the title compound. NMR (300 MHz, CDCl3) δ 8.74 (1H, s,), 8.36 (1H, d, J=8 Hz), 7.50 (1 H, d, J=8 Hz), 4.00 (3H, s), 2.58 (3H, s).

Workup

  1. custompartitioned with ethyl acetate and water
  2. additionPotassium permanganate (0.57 g) was added to the water layer
  3. customresulting solution
  4. stirringwas stirred for 45 minutes
  5. stirringmixture was stirred slowly
  6. customThe toluene layer was separated
  7. washwashed with saturated sodium chloride
  8. dry with materialdried over magnesium sulfate
  9. concentrationconcentrated in vacuo
  10. customto afford the crude product
  11. customPurification on silica gel with hexane/ethyl acetate 7/3

Sources & evidence

ORD record
ord-7b3e61cbf33741d29f4f291e34fe14e3
Source dataset
uspto-grants-1997_05
Patent number
US05631280

Reaction notes

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