Acetic Acid → tert-Butyl 4-(1-(4-aminonaphthalen-1-yloxy)propan-2-yl)pyridin-2-ylcarbamate

HRID 2069061Notes

Reaction equation

HRID 2069061 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][CH:16]([C:18]2[CH:23]=[CH:22][N:21]=[C:20]([NH:24][C:25](=[O:31])[O:26][C:27]([CH3:30])([CH3:29])[CH3:28])[CH:19]=2)[CH3:17])=[CH:6][CH:5]=1)([O-])=O.CC(O)=O.CCOC(C)=O.[H][H]>CO.[Pt]>[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][CH:16]([C:18]2[CH:23]=[CH:22][N:21]=[C:20]([NH:24][C:25](=[O:31])[O:26][C:27]([CH3:30])([CH3:29])[CH3:28])[CH:19]=2)[CH3:17])=[CH:6][CH:5]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 8857Ethyl AcetateHCID 58532579tert-Butyl 4-(1-(4-nitronaphthalen-1-yloxy)propan-2-yl)pyridin-2-ylcarbamateHCID 178418361HCID 178418361, compound

Product 1

HCID 58532582tert-Butyl 4-(1-(4-aminonaphthalen-1-yloxy)propan-2-yl)pyridin-2-ylcarbamateYield 107.6%

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 887MethanolSolvent

Procedure

A solution of the nitroarene (54) (0.61 g, 1.441 mmol) in a mixture of MeOH (20.0 mL), AcOH (5.0 mL) and EtOAc (10.0 mL) was passed through a Thales H-Cube (1.0 mL·min−1, 45° C., 55 mm, 10% Pt/C Cat-Cart, full hydrogen mode). The solvent was evaporated in vacuo and the residue was partitioned between saturated aqueous NaHCO3 solution and EtOAc. The organic layer was washed with water and brine and then dried (MgSO4) and evaporated in vacuo to furnish the title compound (55) (0.61 g, 97%): m/z 394 (M+H)+ (ES+).

Workup

  1. customThe solvent was evaporated in vacuo
  2. customthe residue was partitioned between saturated aqueous NaHCO3 solution and EtOAc
  3. washThe organic layer was washed with water and brine
  4. dry with materialdried (MgSO4)
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-e0487f5068474bd182e0553a7081f50e
Source dataset
uspto-grants-2012_10
Patent number
US08299073B2

Reaction notes

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