HCID 70298247, compound → HCID 70295985, compound

HRID 1421850Notes

Reaction equation

HRID 1421850 reaction equation
[F:1][C:2]1[CH:11]=[CH:10][C:5]2[CH:6]([CH3:9])[NH:7][O:8][C:4]=2[C:3]=1[NH:12]C(=O)OC(C)(C)C>FC(F)(F)C(O)=O>[NH2:12][C:3]1[C:4]2[O:8][NH:7][CH:6]([CH3:9])[C:5]=2[CH:10]=[CH:11][C:2]=1[F:1]

Participants

3

Reactant 1

HCID 70298247HCID 70298247, compound

Product 1

HCID 70295985HCID 70295985, compoundYield 111.7%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

Trifluoroacetic acid (50 mL) was stirred and cooled in an ice-water bath. To this was added t-butyl N-(6-fluoro-3-methyl-1,2(2H)-benzisoxazol-7-yl)carbamate (3.0 g). Upon completion of addition, the reaction mixture was stirred for one hour and then concentrated to a residue. The residue was taken up in water and made basic to pH 8 with sodium bicarbonate. The mixture was then extracted thoroughly with methylene chloride. The combined extracts were washed with water, dried with magnesium sulfate, and concentrated, yielding 2.1 grams of 7-amino-6-fluoro-3-methyl-1,2(2H)-benzisoxazole. The NMR spectrum was consistent with the proposed structure.

Workup

  1. temperaturecooled in an ice-water bath
  2. additionUpon completion of addition
  3. concentrationconcentrated to a residue
  4. extractionThe mixture was then extracted thoroughly with methylene chloride
  5. washThe combined extracts were washed with water
  6. dry with materialdried with magnesium sulfate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-4151098f05254487b1d9f65350bac479
Source dataset
uspto-grants-2000_06
Patent number
US06080702

Reaction notes

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