Water → 2-Tert-butoxy-8-nitro-3,6,7-trichloroquinoxaline

HRID 1060574Notes

Reaction equation

HRID 1060574 reaction equation
[N+:1]([C:4]1[C:13]([Cl:14])=[C:12]([Cl:15])[CH:11]=[C:10]2[C:5]=1[N:6]=[C:7](Cl)[C:8]([Cl:16])=[N:9]2)([O-:3])=[O:2].[CH3:18][C:19]([CH3:22])([O-:21])[CH3:20].[K+].C1(C)C=CC=CC=1.O>C(O)(C)(C)C>[C:19]([O:21][C:7]1[C:8]([Cl:16])=[N:9][C:10]2[C:5](=[C:4]([N+:1]([O-:3])=[O:2])[C:13]([Cl:14])=[C:12]([Cl:15])[CH:11]=2)[N:6]=1)([CH3:22])([CH3:20])[CH3:18]

Participants

6

Reactant 4

HCID 962WaterHCID 1140TolueneHCID 107575382,3,6,7-Tetrachloro-5-nitro-quinoxalineHCID 23665647Potassium tert-butoxide

Product 1

HCID 186291982-Tert-butoxy-8-nitro-3,6,7-trichloroquinoxalineYield 60.6%

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Conditions

Temperature
0 °C

Procedure

To 5-nitro-2,3,6,7-tetrachloroquinoxaline 1608 mg obtained in Example 7(1), was added dropwise a solution of potassium tert-butoxide 644 mg in tert-butanol (15 mL) at −5 to 0° C. The reaction mixture was stirred at 0° C. for 30 min, and toluene 50 mL, 0.1 M sodium dihydrogen phosphate 5 mL, and water were added thereto with shaking. The organic layer was separated, washed with water and saturated saline, and dried over MgSO4. After evaporation, the residue was subjected to column chromato (silica gel/toluene) and crystallized from acetone, to give the title compound (colorless crystal) 1092 mg.

Workup

  1. stirringwith shaking
  2. customThe organic layer was separated
  3. washwashed with water and saturated saline
  4. dry with materialdried over MgSO4
  5. customAfter evaporation
  6. customcrystallized from acetone

Sources & evidence

ORD record
ord-478288073e6241509b41fd8c4ac649e5
Source dataset
uspto-grants-2003_02
Patent number
US06525054B1

Reaction notes

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