Sodium Hydroxide → 2,2,7-Trimethyl-1,3-dioxolo-[4,5-g]-quinoxaline-6-carboxylic acid, 1,1-dimethylethyl ester

HRID 37361Notes

Reaction equation

HRID 37361 reaction equation
[NH2:1][C:2]1[C:12]([NH2:13])=[CH:11][C:5]2[O:6][C:7]([CH3:10])([CH3:9])[O:8][C:4]=2[CH:3]=1.C1(N)C(F)=C(F)C(F)=C(N)C=1F.Cl.Cl.[OH-].[Na+].[C:30]([O:34][C:35](=[O:41])[C:36](=O)[C:37](=O)[CH3:38])([CH3:33])([CH3:32])[CH3:31]>O.O1CCCC1>[CH3:9][C:7]1([CH3:10])[O:6][C:5]2=[CH:11][C:12]3[N:13]=[C:37]([CH3:38])[C:36]([C:35]([O:34][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:41])=[N:1][C:2]=3[CH:3]=[C:4]2[O:8]1

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 149026Tetrafluoro-m-phenylenediamine dihydrochlorideHCID 10986731Tert-butyl 2,3-dioxobutanoateHCID 13343758HCID 13343758, compound

Product 1

HCID 540074732,2,7-Trimethyl-1,3-dioxolo-[4,5-g]-quinoxaline-6-carboxylic acid, 1,1-dimethylethyl ester

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

[5,6-diamino-2,2-dimethyl-1,3-benzodioxole; dihydrochloride salt] (U.S. Pat. No. 4,904,775, Example 3D) (6.8 g, 0.02 mmol) was dissolved in a mixture of 25 ml water and 10 ml tetrahydrofuran and the pH of the solution was adjusted to 5.5 by the addition of 2N NaOH. After addition of the compound from Example 1 (3.8 g; 0.02 mol) the mixture was refluxed for 2 hours, concentrated in vacuo to remove the organic solvent tetrahydrofuran and then extracted with ethyl acetate. The combined organic phases were washed with brine, dried (Na2SO4) and then evaporated in vacuo to leave an oil which crystallized by the addition of petroleum ether.

Workup

  1. temperaturewas refluxed for 2 hours
  2. concentrationconcentrated in vacuo
  3. customto remove the organic solvent tetrahydrofuran
  4. extractionextracted with ethyl acetate
  5. washThe combined organic phases were washed with brine
  6. dry with materialdried (Na2SO4)
  7. customevaporated in vacuo
  8. customto leave an oil which
  9. customcrystallized by the addition of petroleum ether

Sources & evidence

ORD record
ord-74279f6f2f9b4667ac8c0d77abae0991
Source dataset
uspto-grants-1995_05
Patent number
US05420277

Reaction notes

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