(3-Amino-5-ethoxy-4-iodo-phenyl)-methanol → 3-Amino-5-ethoxy-4-iodo-benzaldehyde

HRID 1990833Notes

Reaction equation

HRID 1990833 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH2:12][OH:13])[CH:5]=[C:6]([O:9][CH2:10][CH3:11])[C:7]=1[I:8]>ClCCl.O=[Mn]=O>[NH2:1][C:2]1[CH:3]=[C:4]([CH:5]=[C:6]([O:9][CH2:10][CH3:11])[C:7]=1[I:8])[CH:12]=[O:13]

Participants

4

Reactant 1

HCID 68454929(3-Amino-5-ethoxy-4-iodo-phenyl)-methanol

Product 1

HCID 587063533-Amino-5-ethoxy-4-iodo-benzaldehydeYield 64.5%

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of (3-amino-5-ethoxy-4-iodo-phenyl)-methanol (4.9 g, 16.72 mmol, 1.0 equiv) in dichloromethane (100 mL) was added activated MnO2 (7.27 g, 83.59 mmol, 5.0 equiv) and the reaction mixture heated to reflux for 3 h. Filtration through Hyflo Super Cel, concentration by evaporation under reduced pressure and purification with column chromatography on silica eluting with hexane/ethyl acetate (3:1) yielded 3.14 g (60%) of the title compound. 1H NMR (300 MHz, DMSO): δ 1.37 (t, J=7.0 Hz, 3H), 4.15 (q, J=7.0 Hz, 2H), 4.49 (d, J=5.6 Hz, 2H), 5.21 (t, J=5.6 Hz, 1H), 6.82 (s, 1H), 6.85 (s, 1H), 11.64 (br s, 1H). 13C NMR (75 MHz, DMSO): δ 14.61, 62.89, 64.26, 100.74, 106.46, 117.80, 137.50, 142.74, 144.05, 154.54. MS (ISP): 291.9 [M+H]+.

Workup

  1. temperaturethe reaction mixture heated
  2. temperatureto reflux for 3 h
  3. filtrationFiltration
  4. concentrationthrough Hyflo Super Cel, concentration
  5. customby evaporation
  6. customunder reduced pressure and purification with column chromatography on silica eluting with hexane/ethyl acetate (3:1)

Sources & evidence

ORD record
ord-e88486c99e6e4cf5b4a4565d32a444ad
Source dataset
uspto-grants-2010_01
Patent number
US07645753B2

Reaction notes

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