Sodium Carbonate → tert-butyl 5-oxido-10,11-dihydropyrazino[1',2':1,2]imidazo[4,5-c]quinoline-9(8H)-carboxylate

HRID 1364030Notes

Reaction equation

HRID 1364030 reaction equation
C1C=C(Cl)C=C(C(OO)=[O:9])C=1.[CH:12]1[CH:21]=[CH:20][CH:19]=[C:18]2[C:13]=1[C:14]1[N:24]3[CH2:25][CH2:26][N:27]([C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[CH2:28][C:23]3=[N:22][C:15]=1[CH:16]=[N:17]2.C(=O)([O-])[O-].[Na+].[Na+]>C(Cl)(Cl)Cl>[O-:9][N+:17]1[C:18]2[C:13](=[CH:12][CH:21]=[CH:20][CH:19]=2)[C:14]2[N:24]3[CH2:25][CH2:26][N:27]([C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[CH2:28][C:23]3=[N:22][C:15]=2[CH:16]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 70297m-Chloroperbenzoic acidHCID 66958138tert-butyl 10,11-dihydropyrazino[1',2':1,2]imidazo[4,5-c]quinoline-9(8H)-carboxylate

Product 1

HCID 66958567tert-butyl 5-oxido-10,11-dihydropyrazino[1',2':1,2]imidazo[4,5-c]quinoline-9(8H)-carboxylateYield 91.9%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

mCPBA (26.1 g of 77% pure material, 118 mmol) was added in small portions to a solution of tert-butyl 10,11-dihydropyrazino[1′,2′:1,2]imidazo[4,5-c]quinoline-9(8H)-carboxylate (29.54 g, 91.06 mmol) in chloroform (500 mL), and the reaction was stirred for one hour at ambient temperature. Aqueous sodium carbonate (400 mL of a 1% solution) was added, and the mixture was stirred for 30 minutes. The organic layer was separated, washed with 1% aqueous sodium carbonate (2×300 mL). Citric acid (10% aqueous solution) was added to aid in the separation. The organic layer was then washed twice with 10% aqueous citric acid, and the combined aqueous washings were extracted with chloroform (3×150 mL). The combined organic fractions were dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The resulting solid was dried overnight under vacuum to provide 28.49 g of tert-butyl 5-oxido-10,11-dihydropyrazino[1′,2′:1,2]imidazo[4,5-c]quinoline-9(8H)-carboxylate as a brown solid.

Workup

  1. stirringthe mixture was stirred for 30 minutes
  2. customThe organic layer was separated
  3. washwashed with 1% aqueous sodium carbonate (2×300 mL)
  4. additionCitric acid (10% aqueous solution) was added to aid in the separation
  5. washThe organic layer was then washed twice with 10% aqueous citric acid
  6. extractionthe combined aqueous washings were extracted with chloroform (3×150 mL)
  7. dry with materialThe combined organic fractions were dried over magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure
  10. customThe resulting solid was dried overnight under vacuum

Sources & evidence

ORD record
ord-51c76fa7e4c04b1d916cf71a464a28aa
Source dataset
uspto-grants-2011_02
Patent number
US07888349B2

Reaction notes

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