Dimethylmaleic anhydride → HCID 22402905, compound

HRID 259677Notes

Reaction equation

HRID 259677 reaction equation
[NH2:1][C:2]1[C:3]([F:17])=[CH:4][C:5]2[O:9][N:8]=[C:7]([CH:10]([CH3:15])[C:11]([O:13][CH3:14])=[O:12])[C:6]=2[CH:16]=1.[CH3:18][C:19]1[C:20]([O:22][C:23](=O)[C:24]=1[CH3:25])=[O:21]>C(O)(=O)C>[CH3:25][C:24]1[C:23](=[O:22])[N:1]([C:2]2[C:3]([F:17])=[CH:4][C:5]3[O:9][N:8]=[C:7]([CH:10]([CH3:15])[C:11]([O:13][CH3:14])=[O:12])[C:6]=3[CH:16]=2)[C:20](=[O:21])[C:19]=1[CH3:18]

Participants

4

Reactant 2

HCID 13010Dimethylmaleic anhydrideHCID 22402912HCID 22402912, compound

Product 1

HCID 22402905HCID 22402905, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of methyl 5-amino-6-fluoro-α-methyl-1,2-benzisoxazole-3-acetate (2.6 g, 11.0 mmol) in acetic acid is added to 2,3-dimethylmaleic anhydride (1.39 g, 11.0 mmol). The reaction mixture is refluxed for several hours and concentrated in vacuo to obtain a brown oil. A solution of the oil in ether is washed sequentially with sodium hydrogen carbonate solution and brine, dried over anhydrous sodium sulfate and concentrated in vacuo to obtain a brown oil. Column chromatography of the oil using silica gel and ether/hexanes solutions gives the title product as a white solid, mp 106°-107° C.

Workup

  1. temperatureThe reaction mixture is refluxed for several hours
  2. concentrationconcentrated in vacuo
  3. customto obtain a brown oil
  4. washA solution of the oil in ether is washed sequentially with sodium hydrogen carbonate solution and brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customto obtain a brown oil

Sources & evidence

ORD record
ord-106cbbfd69344393ae98e96288adc8c2
Source dataset
uspto-grants-1996_06
Patent number
US05523278

Reaction notes

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