m-Chloroperbenzoic acid → 9,10-dihydro-8H-[1,2]oxazino[2',3':1,2]imidazo[4,5-c][1,5]naphthyridine 5-oxide

HRID 415520Notes

Reaction equation

HRID 415520 reaction equation
ClC1C=C(C=CC=1)C(OO)=[O:6].[N:12]1[CH:21]=[CH:20][CH:19]=[C:18]2[C:13]=1[C:14]1[N:24]3[O:25][CH2:26][CH2:27][CH2:28][C:23]3=[N:22][C:15]=1[CH:16]=[N:17]2>ClCCl>[N:12]1[CH:21]=[CH:20][CH:19]=[C:18]2[C:13]=1[C:14]1[N:24]3[O:25][CH2:26][CH2:27][CH2:28][C:23]3=[N:22][C:15]=1[CH:16]=[N+:17]2[O-:6]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 666198299,10-dihydro-8H-[1,2]oxazino[2',3':1,2]imidazo[4,5-c][1,5]naphthyridine

Product 1

HCID 666198439,10-dihydro-8H-[1,2]oxazino[2',3':1,2]imidazo[4,5-c][1,5]naphthyridine 5-oxideYield 89.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Solid 3-chloroperoxybenzoic acid (0.26 g of approximately 77% pure material, 1.1 mmol) was added to a solution of 9,10-dihydro-8H-[1,2]oxazino[2′,3′:1,2]imidazo[4,5-c][1,5]naphthyridine (0.13 g, 0.6 mmol) in dichloromethane (15 mL). The reaction was stirred at room temperature for 1 hour and then washed with saturated aqueous sodium carbonate (10 mL). The aqueous fraction was extracted 5 times with 25 mL portions of dichloromethane. The combined organic fractions were dried over potassium carbonate, filtered, and concentrated under reduced pressure to provide 9,10-dihydro-8H-[1,2]oxazino[2′,3′:1,2]imidazo[4,5-c][1,5]naphthyridine 5-oxide (0.13 g).

Workup

  1. washwashed with saturated aqueous sodium carbonate (10 mL)
  2. extractionThe aqueous fraction was extracted 5 times with 25 mL portions of dichloromethane
  3. dry with materialThe combined organic fractions were dried over potassium carbonate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-5ee8ba591498474893abc3131e6fe646
Source dataset
uspto-grants-2012_01
Patent number
US08088788B2

Reaction notes

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