Acetic Acid → 2-Iodo-4-methoxyphenylamine

HRID 541904

Reaktionsgleichung

Reaktionsgleichung von HRID 541904
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N+:9]([O-])=O)=[C:5]([I:12])[CH:4]=1.C(O)(=O)C>CO.O.[Fe]>[I:12][C:5]1[CH:4]=[C:3]([O:2][CH3:1])[CH:8]=[CH:7][C:6]=1[NH2:9]

Komponenten

6

Edukt 2

HCID 176Acetic AcidHCID 27334564-Nitro-3-iodoanisole

Produkt 1

HCID 110103362-Iodo-4-methoxyphenylamineAusbeute 90 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 23925IronKatalysatorHCID 887MethanolLösungsmittelHCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

To a suspension of 3-iodo-4-nitrophenyl methyl ether (5.0 g, 0.018 mol) in methanol (50 mL), water (5 mL), and acetic acid (10 mL) was added iron (3.00 g, 0.0538 mol) powder in small quantities. When the addition was completed, the reaction mixture was heated at 70° C. overnight. After filtration, the cake was rinsed with EtOAc. The filtrate was concentrated and the residue was diluted with NaHCO3 (aq) and EtOAc. After layer separation, the organic layer was dried, filtered and concentrated to give the desired product (4.0 g, 90%).

Aufarbeitung

  1. additionWhen the addition
  2. filtrationAfter filtration
  3. washthe cake was rinsed with EtOAc
  4. concentrationThe filtrate was concentrated
  5. additionthe residue was diluted with NaHCO3 (aq) and EtOAc
  6. customAfter layer separation
  7. customthe organic layer was dried
  8. filtrationfiltered
  9. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-83834a3d830940cea459d854688122b5
Quelldatensatz
uspto-grants-2014_10
Patentnummer
US08871753B2

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