Ethanol → 2-(2,4-Dichlorophenoxy)aniline

HRID 1642219Notes

Reaction equation

HRID 1642219 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[O:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[N+:16]([O-])=O.CCO.[Cl-].[NH4+]>[Fe].O>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[O:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[NH2:16]

Participants

6

Reactant 3

HCID 702EthanolHCID 25517Ammonium ChlorideHCID 7759752,4-Dichloro-1-(2-nitrophenoxy)benzene

Product 1

HCID 968292-(2,4-Dichlorophenoxy)aniline

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 962WaterSolvent

Procedure

2,4-Dichloro-1-(2-nitro-phenoxy)-benzene (HVB01093, 3.7 g, 12 mmol) was added to a refluxing solution of EtOH (55 ml), water (5.5 ml), iron powder (3.7 g, 66 mmol) and ammonium chloride (0.45 g, 8.4 mmol), and stirred at reflux for 4 h. The resulting solution was filtered and evaporated in-vacuo. NaHCO3 was added and extracted with DCM, organic layers dried over MgSO4 and evaporated to dryness. 2.98 g, 96%, Rf. 0.60 (DCM), LCMS tr=4.63 min (50% MeOH and 50% water at 0.5 ml/min), m/z M+H 254.27, 256.29, HPLC tr=2.51 min (Isocratic 90% acetonitrile and 10% water at 1.0 ml/min), 96%, 1HNMR (CDCl3, 270 MHz) δ 3.82 (1H, s, NH), 6.71 (1H, td, J=1.5, 7.6 Hz, ArH), 6.79 (1H, d, J=8.7 Hz, ArH), 6.81 (2H, m, ArH), 7.00 (1H, m, ArH), 7.12 (1H, dd, J=2.5, 8.7 Hz, ArH), 7.44 (1H, d, J=2.5 Hz, ArH),

Workup

  1. temperatureat reflux for 4 h
  2. filtrationThe resulting solution was filtered
  3. customevaporated in-vacuo
  4. additionNaHCO3 was added
  5. extractionextracted with DCM, organic layers
  6. dry with materialdried over MgSO4
  7. customevaporated to dryness
  8. custom0.60 (DCM), LCMS tr=4.63 min (50% MeOH and 50% water at 0.5 ml/min), m/z M+H 254.27, 256.29, HPLC tr=2.51 min (Isocratic 90% acetonitrile and 10% water at 1.0 ml/min), 96%, 1HNMR (CDCl3, 270 MHz) δ 3.82 (1H, s, NH), 6.71 (1H, td, J=1.5, 7.6 Hz, ArH), 6.79 (1H, d, J=8.7 Hz, ArH), 6.81 (2H, m, ArH), 7.00 (1H, m, ArH), 7.12 (1H, dd, J=2.5, 8.7 Hz, ArH), 7.44 (1H, d, J=2.5 Hz, ArH)

Sources & evidence

ORD record
ord-6e71525190f34e9ba183e37c34c0841b
Source dataset
uspto-grants-2012_02
Patent number
US08119627B2

Reaction notes

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