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

HRID 1894904Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1894904
[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-74a137b31200435abdca8cf2f79013da
Quelldatensatz
uspto-grants-2013_08
Patentnummer
US08513270B2

Notizen zur Reaktion

Wird geladen…