Acetic Acid → HCID 59163334, compound

HRID 1879116Notes

Reaction equation

HRID 1879116 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-])=O)=[CH:4][C:3]=1[C:11]([NH:13][C:14]1[CH:19]=[CH:18][C:17]([CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:16][CH:15]=1)=[O:12].C(O)(=O)C>CCO.[Fe]>[NH2:8][C:5]1[CH:6]=[CH:7][C:2]([Cl:1])=[C:3]([C:11]([NH:13][C:14]2[CH:19]=[CH:18][C:17]([CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:16][CH:15]=2)=[O:12])[CH:4]=1

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 59163380HCID 59163380, compound

Product 1

HCID 59163334HCID 59163334, compoundYield 85.9%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

A solution of ethyl (4-{[(2-chloro-5-nitrophenyl)carbonyl]amino}phenyl)acetate (2.27 g, 6.3 mmol) in EtOH (20 ml) was heated at 50° C. A 20% aqueous solution of acetic acid (10 ml) was added followed by iron (6 eq, 37.6 mmol, 2.1 g). The mixture was heated at 80° C. for 30 minutes. On cooling the mixture was filtered through celite washing with EtOH. Solvent evaporated in vacuo. Residue taken up in EtOAc and aqueous sodium bicarbonate. Layers separated, aqueous layer extracted with EtOAc (×2). Organic layers combined and washed with brine, dried over magnesium sulphate and evaporated. The residue was purified by column chromatography (Biotage SP4, 100 g silica column) eluting with 25-75% ethyl acetate in hexanes to afford the title compound as a light yellow oil (1.8 g). MS (ES+) m/z 333 [M+H]+ (C17H1735ClN2O3). 1H-NMR (400 MHz, d6-DMSO) δ 1.18 (3H, m), 3.61 (2H, s), 4.05 (2H, m), 5.47 (2H, s), 6.65 (2H, m), 7.12 (1H, d, J 8.4), 7.22 (2H, d, J 8.4), 7.64 (2H, m).

Workup

  1. temperatureOn cooling the mixture
  2. filtrationwas filtered
  3. washthrough celite washing with EtOH
  4. customSolvent evaporated in vacuo
  5. customLayers separated
  6. extractionaqueous layer extracted with EtOAc (×2)
  7. washwashed with brine
  8. dry with materialdried over magnesium sulphate
  9. customevaporated
  10. customThe residue was purified by column chromatography (Biotage SP4, 100 g silica column)
  11. washeluting with 25-75% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-b4625a05f04e4d94944dc6273c945e0c
Source dataset
uspto-grants-2012_11
Patent number
US08314147B2

Reaction notes

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