6-Nitrochromone → 6-amino-4H-chromen-4-one

HRID 1626165Notes

Reaction equation

HRID 1626165 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[O:10][CH:9]=[CH:8][C:7]2=[O:14])([O-])=O>CO.C(OCC)(=O)C.[Pd]>[NH2:1][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[O:10][CH:9]=[CH:8][C:7]2=[O:14]

Participants

4

Reactant 1

HCID 8477166-Nitrochromone

Product 1

HCID 194388266-amino-4H-chromen-4-oneYield 94%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21584119Ethylacetate methanolSolvent

Procedure

To a solution of 6-nitrochromone (2.0 g, 10.5 mmol) in methanol/ethyl acetate (100 mL/20 mL) purged with argon, was added 5% Pd/C (Degussa-wet, 0.5 g) catalyst. Hydrogen gas was bubbled through the slurry with stirring until (2 hrs.) LCMS and TLC showed complete conversion of starting material to product. The spent palladium catalyst was filtered off through a celite, and the solid was washed with methanol. The combined filtrate and washings were evaporated to produce 6-amino-chromen-4-one (1.58 g, 94%) as a light yellow solid. LCMS m/z (%)=162 (M+H, 100), 1H NMR (400 MHz, CDCl3) δ: 7.79 (d, J=5.96 Hz, 1H), 7.38 (d, J=2.86 Hz, 1H), 7.29 (d, J=8.88 Hz, 1H), 7.01 (dd, J=8.80 Hz, 2.8 Hz, 1H), 6.26 (d, J=5.96 Hz, 1H), 5.29 (s, 2H).

Workup

  1. customHydrogen gas was bubbled through the slurry
  2. filtrationThe spent palladium catalyst was filtered off through a celite
  3. washthe solid was washed with methanol
  4. customThe combined filtrate and washings were evaporated

Sources & evidence

ORD record
ord-5b6a611759f349e9993758f43dd6803e
Source dataset
uspto-grants-2014_07
Patent number
US08785441B2

Reaction notes

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