HCID 66617790, compound → HCID 66617677, compound

HRID 226206Notes

Reaction equation

HRID 226206 reaction equation
[CH2:1]1[CH2:3][CH:2]1[CH:4]1[C:9](=[O:10])[N:8](CC2C=CC(OC)=CC=2)[C:7]2[CH:20]=[C:21]([N+:24]([O-:26])=[O:25])[CH:22]=[CH:23][C:6]=2[O:5]1>C(#N)C.O>[CH2:3]1[CH2:1][CH:2]1[CH:4]1[C:9](=[O:10])[NH:8][C:7]2[CH:20]=[C:21]([N+:24]([O-:26])=[O:25])[CH:22]=[CH:23][C:6]=2[O:5]1

Participants

3

Reactant 1

HCID 66617790HCID 66617790, compound

Product 1

HCID 66617677HCID 66617677, compoundYield 94.6%

Reagents, catalysts & solvents 1

HCID 18373917Acetonitrile--water (1/1)Solvent

Procedure

To solution of 400 mg 2-(2-cyclopropyl)-6-nitro-3-oxo-4-(p-methoxybenzyl)-benz[1,4]oxazine in acetonitrile/water (50 mL) was added 2.5 eq of ceric ammonium nitrate. The reaction mixture was stirred at ambient temperature for 18 hour, filtered, concentrated and the resulting residue partitioned between bicarbonate solution and EtOAc. The aqueous phase was extracted with EtOAc and the combined organics washed with water, brine and then dried over MgSO4. The solvent was removed in vacuo and the crude material purified by column chromatography (hexanes/EtOAc) to yield 250 mg of the desired product 2-(2-cyclopropyl)-6-nitro-3-oxo-4H-benz[1,4]oxazine. MS (m/e): 341 (MH+).

Workup

  1. filtrationfiltered
  2. concentrationconcentrated
  3. customthe resulting residue partitioned between bicarbonate solution and EtOAc
  4. extractionThe aqueous phase was extracted with EtOAc
  5. washthe combined organics washed with water, brine
  6. dry with materialdried over MgSO4
  7. customThe solvent was removed in vacuo
  8. customthe crude material purified by column chromatography (hexanes/EtOAc)

Sources & evidence

ORD record
ord-5bac8dc86e3b4385b2eb4fc73ddfd288
Source dataset
uspto-grants-2009_07
Patent number
US07557207B2

Reaction notes

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