Acetic Anhydride → acetic acid 3-azido-2-oxo-2H-chromen-7-yl ester

HRID 19454Notes

Reaction equation

HRID 19454 reaction equation
[N:1]([C:4]1[C:5](=[O:15])[O:6][C:7]2[C:12]([CH:13]=1)=[CH:11][CH:10]=[C:9]([OH:14])[CH:8]=2)=[N+:2]=[N-:3].[C:16](OC(=O)C)(=[O:18])[CH3:17]>C(Cl)Cl.N1C=CC=CC=1>[N:1]([C:4]1[C:5](=[O:15])[O:6][C:7]2[C:12]([CH:13]=1)=[CH:11][CH:10]=[C:9]([O:14][C:16](=[O:18])[CH3:17])[CH:8]=2)=[N+:2]=[N-:3]

Participants

5

Reactant 2

HCID 7918Acetic AnhydrideHCID 251276083-Azido-7-hydroxycoumarin

Product 1

HCID 86019028acetic acid 3-azido-2-oxo-2H-chromen-7-yl esterYield 86%

Reagents, catalysts & solvents 2

HCID 1049PyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a stirred suspension of 3-azido-7-hydroxycoumarin (203 mg, 1.0 mmol) in dry CH2Cl2 (15 mL), acetic anhydride (1.5 mmol) and pyridine (one drop) were added. Upon stirring overnight at room temperature, the solvent was removed under reduced pressure. The residue was dissolved in ethyl acetate and washed with H2O. The organic layer was dried over anhydrous Na2SO4 and concentrated. Purification with column chromatography over silica gel (hexane-EtOAc 4:1) afforded the final product as a yellow solid (210 mg, 86%). 1H-NMR (DMSO-d6, 300 MHz) δ 2.29 (s, 3H), 7.17 (dd, J=8.0, 2.0 Hz, 1H), 7.32 (d, J=2.1 Hz, 1H), 7.67 (s, 1H), 7.70 (d, J=7.9 Hz, 1H). 13C NMR (DMSO-d6, 75 MHz) δ 21.5, 110.6, 117.8, 119.9, 125.8, 126.8, 129.2, 151.9, 152.3, 157.5, 169.6. IR (KBr): 2133 (vs), 1749, 1730 (vs), 1622 (s), 1234 (s). EI-HRMS m/e calculated for M+ C11H7N3O4 245.0437; found 245.0432.

Workup

  1. additionwere added
  2. customthe solvent was removed under reduced pressure
  3. dissolutionThe residue was dissolved in ethyl acetate
  4. washwashed with H2O
  5. dry with materialThe organic layer was dried over anhydrous Na2SO4
  6. concentrationconcentrated
  7. customPurification with column chromatography over silica gel (hexane-EtOAc 4:1)

Sources & evidence

ORD record
ord-b78703caaa0c49c3ad5dea1adc770722
Source dataset
uspto-grants-2010_06
Patent number
US07745229B2

Reaction notes

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