Acetic Anhydride → HCID 90384168, compound

HRID 928669Notes

Reaction equation

HRID 928669 reaction equation
[Br:1][C:2]1[C:10]2[O:9][CH:8]=[C:7]([CH:11]=O)[C:6]=2[C:5]([F:13])=[C:4]([F:14])[CH:3]=1.C([O-])(=O)C.[Na+].Cl.[NH2:21]O.C(OC(=O)C)(=O)C>C(O)(=O)C>[Br:1][C:2]1[C:10]2[O:9][CH:8]=[C:7]([C:11]#[N:21])[C:6]=2[C:5]([F:13])=[C:4]([F:14])[CH:3]=1

Participants

6

Reactant 4

HCID 7918Acetic AnhydrideHCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 90384304HCID 90384304, compound

Product 1

HCID 90384168HCID 90384168, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
60 °C

Procedure

The compound (360 mg, 1.38 mmol) obtained in Step 3 was dissolved in acetic acid (5 mL), and sodium acetate (450 mg, 5.5 mmol) and hydroxylamine hydrochloride (140 mg, 2.1 mmol) were added thereto, and stirred at 60° C. for 2 hours. After that, acetic anhydride (0.26 mL, 2.75 mmol) was added thereto, and stirred at 100° C. for 2 hours. After cooling, the solvent was distilled away, and the resulting residue was purified by silica gel chromatography (hexane/ethyl acetate) to thus obtain the title compound.

Workup

  1. stirringstirred at 100° C. for 2 hours
  2. temperatureAfter cooling
  3. distillationthe solvent was distilled away
  4. customthe resulting residue was purified by silica gel chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-c2054f59a273412291e416ae0f495b0f
Source dataset
uspto-grants-2016_03
Patent number
US09290487B2

Reaction notes

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