Formic Acid → HCID 86612341, compound

HRID 1787109Notes

Reaction equation

HRID 1787109 reaction equation
[NH2:1][C:2]1[C:13]([CH3:14])=[C:12]([CH3:15])[C:5]2[C:6](=[O:11])[C:7]([CH3:10])([CH3:9])[O:8][C:4]=2[C:3]=1[CH3:16].[CH:17](O)=[O:18]>>[CH3:10][C:7]1([CH3:9])[C:6](=[O:11])[C:5]2[C:12]([CH3:15])=[C:13]([CH3:14])[C:2]([NH:1][CH:17]=[O:18])=[C:3]([CH3:16])[C:4]=2[O:8]1

Participants

3

Reactant 2

HCID 284Formic AcidHCID 23114289HCID 23114289, compound

Product 1

HCID 86612341HCID 86612341, compoundYield 81%

Procedure

A mixture of formic acid (5 mL) with 6-amino-2,2,4,5,7-pentamethyl-1-benzofuran-3(2H)-one (700 mg, 3.19 mmol) obtained in Reference Example 72, was heated under reflux for 5 hours. The solvent was distilled off under reduced pressure, water and ethyl acetate were added to the residue, and the aqueous layer was extracted with ethyl acetate. The combined organic layer was washed with water and a saturated sodium hydrogen carbonate solution, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure. The obtained residue was crystallized from hexane-ethyl acetate to obtain 640 mg (yield 81%) of the title compound. Melting point: 191-192° C.

Workup

  1. customobtained in Reference Example 72
  2. temperaturewas heated
  3. temperatureunder reflux for 5 hours
  4. distillationThe solvent was distilled off under reduced pressure, water and ethyl acetate
  5. additionwere added to the residue
  6. extractionthe aqueous layer was extracted with ethyl acetate
  7. washThe combined organic layer was washed with water
  8. dry with materiala saturated sodium hydrogen carbonate solution, dried over anhydrous sodium sulfate
  9. concentrationconcentrated under reduced pressure
  10. customThe obtained residue was crystallized from hexane-ethyl acetate

Sources & evidence

ORD record
ord-a4969a7af16644b7a01aa9a3133f17ea
Source dataset
uspto-grants-2009_03
Patent number
US07507841B2

Reaction notes

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