Acetic Anhydride → HCID 21874908, compound

HRID 723648Notes

Reaction equation

HRID 723648 reaction equation
[F:1][C:2]1[C:11]2[C:6](=[C:7]([N+:12]([O-])=O)[CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][CH:3]=1.[CH3:15][C:16](OC(C)=O)=[O:17]>CC(O)=O.[Fe]>[F:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[CH:10]=[CH:9][CH:8]=[C:7]2[NH:12][C:16](=[O:17])[CH3:15]

Participants

5

Reactant 2

HCID 7918Acetic AnhydrideHCID 217302841-Fluoro-5-nitronaphthalene

Product 1

HCID 21874908HCID 21874908, compoundYield 97%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 176Acetic AcidSolvent

Procedure

A solution of 141 mg (0.74 mmol) of compound 208A in 2 mL of AcOH was heated to reflux and treated with small portions of iron powder (118 mg, 2.11 mmol). The mixture was kept at reflux for 15 min before 73 μL (0.78 mmol) of Ac2O was added. After an additional 15 min at reflux, the mixture was cooled and filtered eluting with CH2Cl2. The filtrate was then concentrated under reduced pressure and the residue was purified by flash chromatography on silica gel eluting with 20 to 50% EtOAc in to give 145 mg (0.71 mmol, 97%) of compound 209A as a white solid.

Workup

  1. temperatureto reflux
  2. additionwas added
  3. temperatureAfter an additional 15 min at reflux
  4. temperaturethe mixture was cooled
  5. filtrationfiltered
  6. washeluting with CH2Cl2
  7. concentrationThe filtrate was then concentrated under reduced pressure
  8. customthe residue was purified by flash chromatography on silica gel eluting with 20 to 50% EtOAc in

Sources & evidence

ORD record
ord-a4e96fe61e094ccfab137f19592e1999
Source dataset
uspto-grants-2006_11
Patent number
US07141578B2

Reaction notes

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