Sodium Bicarbonate → tert-Butyl 4-(2-(4-aminonaphthalen-1-yloxy)ethyl)pyridin-2-ylcarbamate

HRID 1916796Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1916796
[N+:1]([C:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7]([O:14][CH2:15][CH2:16][C:17]2[CH:22]=[CH:21][N:20]=[C:19]([NH:23][C:24](=[O:30])[O:25][C:26]([CH3:29])([CH3:28])[CH3:27])[CH:18]=2)=[CH:6][CH:5]=1)([O-])=O.C([O-])(O)=O.[Na+]>CC(O)=O.CCO.[Fe]>[NH2:1][C:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7]([O:14][CH2:15][CH2:16][C:17]2[CH:22]=[CH:21][N:20]=[C:19]([NH:23][C:24](=[O:30])[O:25][C:26]([CH3:28])([CH3:27])[CH3:29])[CH:18]=2)=[CH:6][CH:5]=1

Komponenten

6

Edukt 2

HCID 516892Sodium BicarbonateHCID 58416756tert-Butyl 4-(2-(4-nitronaphthalen-1-yloxy)ethyl)pyridin-2-ylcarbamate

Produkt 1

HCID 58416770tert-Butyl 4-(2-(4-aminonaphthalen-1-yloxy)ethyl)pyridin-2-ylcarbamateAusbeute 103,8 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 23925IronKatalysatorHCID 176Acetic AcidLösungsmittelHCID 702EthanolLösungsmittel

Versuchsvorschrift

tert-Butyl 4-(2-(4-nitronaphthalen-1-yloxy)ethyl)pyridin-2-ylcarbamate (11) (5.20 g, 12.7 mmol) and iron mesh (4.30 g, 76 mmol) were suspended in a mixture of AcOH and EtOH (1:2, 120 mL). The suspension was placed in a pre-heated oil bath at 60° C. and stirred rapidly until the reaction was judged to be complete by LC-MS. The mixture was cooled to RT, poured carefully onto saturated aq NaHCO3 (1000 mL) and extracted with EtOAc (500 mL×2). The combined organic layers were washed with further saturated aq NaHCO3 (1000 mL), water (1000 mL), brine (1000 mL) and dried. This was filtered and evaporated to give tert-butyl 4-(2-(4-aminonaphthalen-1-yloxy)ethyl)pyridin-2-ylcarbamate (13) as a yellow oil (5.00 g, 95%): m/z 380 (M+H)+ (ES+).

Aufarbeitung

  1. customThe suspension was placed in a pre-heated oil bath at 60° C.
  2. extractionextracted with EtOAc (500 mL×2)
  3. washThe combined organic layers were washed with further saturated aq NaHCO3 (1000 mL), water (1000 mL), brine (1000 mL)
  4. customdried
  5. filtrationThis was filtered
  6. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-c45e4a069fd245599a81b8314fd40441
Quelldatensatz
uspto-grants-2013_12
Patentnummer
US08618140B2

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