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

HRID 872397Notes

Reaction equation

HRID 872397 reaction equation
[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

Participants

6

Reactant 2

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

Product 1

HCID 58416770tert-Butyl 4-(2-(4-aminonaphthalen-1-yloxy)ethyl)pyridin-2-ylcarbamateYield 103.8%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 176Acetic AcidSolventHCID 702EthanolSolvent

Procedure

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+).

Workup

  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

Sources & evidence

ORD record
ord-4ef5a70b1d64461fa6533b438ed3b88c
Source dataset
uspto-grants-2015_03
Patent number
US08975285B2

Reaction notes

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