Iodine → Methyl 6-amino-5-iodo-2-methylnicotinate

HRID 526006Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 526006
I([O-])(=O)(=O)=O.[Na+].[I:7]I.[NH2:9][C:10]1[CH:19]=[CH:18][C:13]([C:14]([O:16][CH3:17])=[O:15])=[C:12]([CH3:20])[N:11]=1.S([O-])([O-])(=O)=S.[Na+].[Na+]>CN(C=O)C.O>[NH2:9][C:10]1[C:19]([I:7])=[CH:18][C:13]([C:14]([O:16][CH3:17])=[O:15])=[C:12]([CH3:20])[N:11]=1

Komponenten

7

Edukt 4

HCID 807IodineHCID 24477Sodium ThiosulfateHCID 23667635Sodium periodateHCID 55252884Methyl 6-amino-2-methylpyridine-3-carboxylate

Produkt 1

HCID 59747893Methyl 6-amino-5-iodo-2-methylnicotinate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

Sodium periodate (4.05 g, 18.9 mmol) and iodine (9.62 g, 37.9 mmol) were added to a solution of methyl 6-amino-2-methylnicotinate (8.40 g, 50.5 mmol) in DMF (45 ml), and the mixture was then stirred at 50° C. for 1.5 hours. The reaction mixture was added to a cold solution of 250 ml of saturated sodium thiosulphate solution in 150 ml of water. The solid formed was filtered off with suction, washed with water and dried. This gave 13.4 mg (88.9% of theory) of methyl 6-amino-5-iodo-2-methylnicotinate. HPLC-MS: log P=1.55; mass (m/z): 293.0 (M+H)+; 1H-NMR (D6DMSO) 2.50 (s, 3H), 3.74 (s, 3H), 6.81 (br. s, 1H), 8.25 (s, 1H).

Aufarbeitung

  1. customThe solid formed
  2. filtrationwas filtered off with suction
  3. washwashed with water
  4. customdried

Quellen und Nachweise

ORD-Eintrag
ord-9a9b0fc43e0b408da246b9ba35be96df
Quelldatensatz
uspto-grants-2016_05
Patentnummer
US09345247B2

Notizen zur Reaktion

Wird geladen…