4-Azido-6-methyl-2H-pyran-2-one → 2H-Pyran-2-one,4-amino-6-methyl-(9CI)

HRID 545655Notes

Reaction equation

HRID 545655 reaction equation
[N:1]([C:4]1[CH:9]=[C:8]([CH3:10])[O:7][C:6](=[O:11])[CH:5]=1)=[N+]=[N-].[H][H]>C(O)C.[Pd]>[NH2:1][C:4]1[CH:9]=[C:8]([CH3:10])[O:7][C:6](=[O:11])[CH:5]=1

Participants

5

Reactant 2

HCID 154994784-Azido-6-methyl-2H-pyran-2-oneHCID 178418361HCID 178418361, compound

Product 1

HCID 110623852H-Pyran-2-one,4-amino-6-methyl-(9CI)Yield 101.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a 0.310 g (2.05 mmol) of 38 and 0.031 g of 10% Pd/C in 10 mL of ethanol was maintained under 1 atm (a ballonn) of hydrogen gas for 1 hour. The reaction mixture was then filtered through Celite, and ethanol of the filtrate was removed through rotary evaporation to give 0.260 g of 39 (100% yield). 1H NMR δ 5.56 (s, 1H, C3H), 5.12 (s, 1H, C5H), 4.45 (s, 2H, NH2), 2.20 (s, Me); 13C NMR δ 163.6 (s, C2), 161.3 (s), 98.6 (d, C5), 80.4 (d, C3), 19.5 (q, Me).

Workup

  1. filtrationThe reaction mixture was then filtered through Celite, and ethanol of the filtrate
  2. customwas removed through rotary evaporation

Sources & evidence

ORD record
ord-082d5b9906584075be4f6b1164e8dc2b
Source dataset
uspto-grants-2011_05
Patent number
US07935726B1

Reaction notes

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