Sodium Carbonate → HCID 67273561, compound

HRID 602264Notes

Reaction equation

HRID 602264 reaction equation
[CH3:1][CH:2]1[C:7]2=[N:8][C:9]3[CH:10]=[N:11][C:12]4[C:17]([C:18]=3[N:6]2[C@@H:5]([CH3:19])[CH2:4][O:3]1)=[CH:16][CH:15]=[CH:14][CH:13]=4.ClC1C=C(C=CC=1)C(OO)=[O:25].C([O-])([O-])=O.[Na+].[Na+]>C(Cl)(Cl)Cl>[CH3:1][CH:2]1[C:7]2=[N:8][C:9]3[CH:10]=[N+:11]([O-:25])[C:12]4[C:17]([C:18]=3[N:6]2[C@@H:5]([CH3:19])[CH2:4][O:3]1)=[CH:16][CH:15]=[CH:14][CH:13]=4

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 70297m-Chloroperbenzoic acidHCID 67273848HCID 67273848, compound

Product 1

HCID 67273561HCID 67273561, compoundYield 99.9%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

A solution of (11S)-8,11-dimethyl-10,11-dihydro-8H-[1,4]oxazino[4′,3′:1,2]imidazo[4,5-c]quinoline (80 mg, 0.316 mmol) and 5 mL of CHCl3 was treated with MCPBA (meta-chloroperoxybenzoic acid) (93 mg, 77% max). After 18 hours, the reaction was treated with ˜10 mL of CHCl3 and 5 mL of 2% Na2CO3 solution and the layers were separated. The aqueous layer was extracted with CHCl3 (5×10 mL). The organic layers were combined then washed with brine, dried over Na2SO4, filtered, and concentrated to give (11S)-8,11-dimethyl-10,11-dihydro-8H-[1,4]oxazino[4′,3′:1,2]imidazo[4,5-c]quinoline 5-oxide (85 mg) as a light yellow solid.

Workup

  1. customthe layers were separated
  2. extractionThe aqueous layer was extracted with CHCl3 (5×10 mL)
  3. washThe organic layers were combined then washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-dd77e688a5b24dfcb204fdd63ba55bb4
Source dataset
uspto-grants-2011_03
Patent number
US07906506B2

Reaction notes

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