Acetic Acid → HCID 19047723, compound

HRID 1780813Notes

Reaction equation

HRID 1780813 reaction equation
[CH3:1][C:2]1[C:7]([CH3:8])=[CH:6][CH:5]=[CH:4][C:3]=1[NH:9][CH2:10][C:11]1[CH:12]=[C:13]([N+:17]([O-])=O)[CH:14]=[CH:15][CH:16]=1.C(O)(=O)C>C(O)C.[Fe]>[CH3:1][C:2]1[C:7]([CH3:8])=[CH:6][CH:5]=[CH:4][C:3]=1[NH:9][CH2:10][C:11]1[CH:12]=[C:13]([CH:14]=[CH:15][CH:16]=1)[NH2:17]

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 19047699HCID 19047699, compound

Product 1

HCID 19047723HCID 19047723, compound

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 702EthanolSolvent

Procedure

To a solution of 15 (0.40 g) in ethanol (8 mL) was added elemental iron (Fe) (0.31 g) and acetic acid (0.66 g). The mixture was refluxed for 18 h. The mixture was filtered, concentrated in vacuo and the residue was partitioned between ethyl acetate and water. The ethyl acetate layer was extracted with saturated sodium bicarbonate, saturated sodium chloride, dried over magnesium sulfate and concentrated in vacuo to afford the title compound as an oil. NMR (300 MHz, CDCl3) δ 7.13 (1H, t, J=3 Hz), 6.99 (1H, t, J=3 Hz), 6.77 (1H, d, J=3 Hz), 6.72 (1H, s), 6.60 (2H, d, J=3 Hz), 6.50 (1H, d, J=3 Hz), 4.25 (2H, s), 3.85 (1H, s), 3.65 (1H, s), 2.29 (3H, s), 2.05 (3H, s).

Workup

  1. temperatureThe mixture was refluxed for 18 h
  2. filtrationThe mixture was filtered
  3. concentrationconcentrated in vacuo
  4. customthe residue was partitioned between ethyl acetate and water
  5. extractionThe ethyl acetate layer was extracted with saturated sodium bicarbonate, saturated sodium chloride
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-65670695cb55427e86f06ce800346705
Source dataset
uspto-grants-1997_05
Patent number
US05631280

Reaction notes

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