Acetic Anhydride → HCID 67406769, compound

HRID 1913428Notes

Reaction equation

HRID 1913428 reaction equation
[CH3:1][O:2][C:3](=[O:16])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[CH:7][C:6]=1[N+:13]([O-])=O.[C:17](OC(=O)C)(=[O:19])[CH3:18]>C(O)(=O)C.[Zn]>[CH3:1][O:2][C:3](=[O:16])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[CH:7][C:6]=1[NH:13][C:17](=[O:19])[CH3:18]

Participants

5

Reactant 2

HCID 7918Acetic AnhydrideHCID 15740597HCID 15740597, compound

Product 1

HCID 67406769HCID 67406769, compoundYield 68%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalyst2×HCID 176Acetic AcidSolvent

Conditions

Temperature
0 °C

Procedure

To a suspension of (4-methoxy-2-nitro-phenyl)-acetic acid methyl ester (154 mg, 0.68 mmol) in 3 mL of acetic acid was added acetic anhydride (3.0 mL, 30.0 mmol) and zinc (nanopowder, 220 mg, 3.36 mmol) in portions over 5 min at 0° C. The reaction mixture was maintained for 30 minutes at 0° C. and 1.5 h at room temperature. Additional zinc powder (110 mg, 1.68 mmol) was added, and the reaction mixture was stirred overnight at room temperature. After filtration, the mixture was partitioned between 50 mL of ethyl acetate and 10 mL of saturated aqueous NaHCO3. The organic layer was washed with brine, dried over Na2SO4 and concentrated in vacuo. The crude product was purified on a Biotage (Biotage Inc.) 10 g silica column, eluted with 0-40% EtOAc in heptane to provide 49 mg (68%) of (2-acetylamino-4-methoxy-phenyl)-acetic acid methyl ester. 1H NMR (CDCl3) δ 2.23 (s, 3H), 3.57 (s, 2H), 3.73 (s, 3H), 3.81 (s, 3H), 6.66 (dd, 1H), 7.09 (d, 1H), 7.57 (d, 1H).

Workup

  1. filtrationAfter filtration
  2. customthe mixture was partitioned between 50 mL of ethyl acetate and 10 mL of saturated aqueous NaHCO3
  3. washThe organic layer was washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe crude product was purified on a Biotage (Biotage Inc.) 10 g silica column
  7. washeluted with 0-40% EtOAc in heptane

Sources & evidence

ORD record
ord-bdce6a8372c9481cbf521da5a2af29e3
Source dataset
uspto-grants-2013_12
Patent number
US08609680B2

Reaction notes

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