Acetic Acid → 5-Iodo-6-methylpyridin-3-amine

HRID 77732Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 77732
[I:1][C:2]1[C:3]([CH3:11])=[N:4][CH:5]=[C:6]([N+:8]([O-])=O)[CH:7]=1.C(O)(=O)C>C(O)C.CCOC(C)=O.O.C([O-])([O-])=O.[Na+].[Na+].[Fe]>[I:1][C:2]1[CH:7]=[C:6]([NH2:8])[CH:5]=[N:4][C:3]=1[CH3:11]

Komponenten

8

Edukt 2

HCID 176Acetic AcidHCID 591983253-Iodo-2-methyl-5-nitropyridine

Produkt 1

HCID 591982915-Iodo-6-methylpyridin-3-amine

Reagenzien, Katalysatoren, Lösungsmittel 5

HCID 23925IronKatalysatorHCID 702EthanolLösungsmittelHCID 962WaterLösungsmittelHCID 8857Ethyl AcetateLösungsmittelHCID 10340Sodium CarbonateLösungsmittel

Reaktionsbedingungen

Temperatur
85 °C

Versuchsvorschrift

To a solution of 3-iodo-2-methyl-5-nitropyridine (125 mg, 0.4734 mmol) in ethanol (3 mL) was added acetic acid (0.50 mL, 8.8 mmol) and iron powder (140 mg, 2.6 mmol). The reaction was heated at 85° C. for 30 minutes and was diluted with EtOAc, water, and saturated Na2CO3. Then it was filtered and extracted with EtOAc and the organic extracts were washed with water, saturated NaCl, dried (MgSO4) and stripped in vacuo. 1H NMR (400 MHz, CDCl3): δ 7.96 (d, 1H), 7.44 (d, 1H), 3.57 (br s, 2H), 2.61 (s, 3H); MS (ES) (M+H)=235.

Aufarbeitung

  1. filtrationThen it was filtered
  2. extractionextracted with EtOAc
  3. washthe organic extracts were washed with water, saturated NaCl
  4. dry with materialdried (MgSO4)

Quellen und Nachweise

ORD-Eintrag
ord-b5498f3055774869b614690be34b85eb
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08841318B2

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