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

HRID 540586Notes

Reaction equation

HRID 540586 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 no starting material. 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 as a light yellow solid (1.58 g, 94%). LCMS m/z (%)=162 (M+H, 100), 1H NMR (400 MHz, CDCl3) δ: 7.79-7.81 (d, J=5.96 Hz, 1H), 7.38 (d, J=2.86 Hz, 1H), 7.29-7.31 (d, J=8.88 Hz, 1H), 7.01-7.04 (dd, J=8.80, 2.8 Hz, 1H), 6.26-6.28 (d, J=5.96 Hz, 1H), 5.299 (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-90e3b7ebe4d0492488b9bfcc1a7a0bec
Source dataset
uspto-grants-2014_10
Patent number
US08871797B2

Reaction notes

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