Furobufen → 4-dibenzofuran-2-yl-4-hydroxyiminobutanoic acid

HRID 1377772Notes

Reaction equation

HRID 1377772 reaction equation
O=[C:2]([C:8]1[CH:20]=[CH:19][C:11]2[O:12][C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[C:10]=2[CH:9]=1)[CH2:3][CH2:4][C:5]([OH:7])=[O:6].[OH2:21].O.O.C([O-])(=O)C.[Na+].Cl.[NH2:30]O>CO.O>[CH:9]1[C:10]2[C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=3[O:12][C:11]=2[CH:19]=[CH:20][C:8]=1[C:2](=[N:30][OH:21])[CH2:3][CH2:4][C:5]([OH:7])=[O:6]

Participants

6

Reactant 3

HCID 38117FurobufenHCID 443297Hydroxyamine hydrochlorideHCID 23665404Sodium Acetate Trihydrate

Product 1

HCID 42264-dibenzofuran-2-yl-4-hydroxyiminobutanoic acidYield 68%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A solution of γ-oxo-2-dibenzofuranbutanoic acid (Example 1) (75.5 g) and sodium acetate trihydrate (114.9 g) in methanol (2.5 L) is treated with a solution of hydroxylamine hydrochloride (38.9 g) in water (150 mL of solution). The solution is heated to reflux for 3.5 hours then concentrated, cooled, and filtered. This solid was washed with water then dried in vacuo to give the crude title compound (71.32 g, 89.6% of theory). This solid was recrystallized from ethyl acetate, washed with hexane, and dried in vacuo to give 53.04 g (68% yield) of the title compound; mp 167-168° C. (d).

Workup

  1. temperatureThe solution is heated
  2. temperatureto reflux for 3.5 hours
  3. concentrationthen concentrated
  4. temperaturecooled
  5. filtrationfiltered
  6. washThis solid was washed with water
  7. customthen dried in vacuo
  8. customto give the crude title compound (71.32 g, 89.6% of theory)
  9. customThis solid was recrystallized from ethyl acetate
  10. washwashed with hexane
  11. customdried in vacuo

Sources & evidence

ORD record
ord-341c309fcc904996acded74ac71bfdd4
Source dataset
uspto-grants-1997_09
Patent number
US05665764

Reaction notes

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