Phenol → HCID 86727432, compound

HRID 519066Notes

Reaction equation

HRID 519066 reaction equation
F[C:2]1[CH:15]=[C:14]2[C:5]([N:6]3[C:11]([CH2:12][O:13]2)=[N:10][NH:9][C:8](=[O:16])[CH:7]3[CH3:17])=[CH:4][C:3]=1[N+:18]([O-:20])=[O:19].C([O-])([O-])=O.[K+].[K+].[C:27]1([OH:33])[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>CC(C)=O>[CH3:17][CH:7]1[N:6]2[C:11]([CH2:12][O:13][C:14]3[C:5]2=[CH:4][C:3]([N+:18]([O-:20])=[O:19])=[C:2]([O:33][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH:15]=3)=[N:10][NH:9][C:8]1=[O:16]

Participants

5

Reactant 3

HCID 996PhenolHCID 11430Potassium CarbonateHCID 86727430HCID 86727430, compound

Product 1

HCID 86727432HCID 86727432, compoundYield 24%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 7-fluoro-4-methyl-6-nitro-2,10-dihydro-9-oxa-1,2,4a-triaza-phenanthren-3-one (0.30 g, 1.07 mmol), K2CO3 (0.296 g, 2.14 mmol) and phenol (0.151 g, 1.61 mmol) in acetone (10 mL) was stirred at ambient temperature for 48 h and then heated to reflux for 3 h. After cooling to ambient temperature, the solvent was removed in vacuo and the residue was partitioned between EtOAc (30 mL) and water (10 mL). The organic portion was washed with brine (10 mL), dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified by chromatography on silical gel (eluting with 15% EtOAc in petroleum ether) to give 4-methyl-6-nitro-7-phenoxy-2,10-dihydro-9-oxa-1,2,4a-triaza-phenanthren-3-one (0.090 g, 24%) as an orange solid. LC/MS (Table 1, Method 2) Rt=1.117 min; MS m/z: 355 [M+H]+

Workup

  1. temperatureheated
  2. temperatureto reflux for 3 h
  3. temperatureAfter cooling to ambient temperature
  4. customthe solvent was removed in vacuo
  5. customthe residue was partitioned between EtOAc (30 mL) and water (10 mL)
  6. washThe organic portion was washed with brine (10 mL)
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customThe residue was purified by chromatography on silical gel (eluting with 15% EtOAc in petroleum ether)

Sources & evidence

ORD record
ord-8288b4497c0c477697bb245666f06f40
Source dataset
uspto-grants-2015_08
Patent number
US09115151B2

Reaction notes

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