Ethyl 7-amino-4-oxo-4H-chromene-2-carboxylate → Ethyl 7-Amino-2-chromancarboxylate

HRID 49459Notes

Reaction equation

HRID 49459 reaction equation
[NH2:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=O)[CH:7]=[C:8]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[O:9]2)=[CH:4][CH:3]=1>C(O)C.Cl.[Pd]>[NH2:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][CH:8]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[O:9]2)=[CH:4][CH:3]=1

Participants

5

Reactant 1

HCID 10728325Ethyl 7-amino-4-oxo-4H-chromene-2-carboxylate

Product 1

HCID 10632774Ethyl 7-Amino-2-chromancarboxylateYield 89%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 313Hydrochloric AcidSolventHCID 702EthanolSolvent

Procedure

A solution of ethyl 7-amino-4-oxo-4H-chromene-2-carboxylate (1.00 g, 4.3 mmol) in ethanol and concentrated HCl (5 mL) is hydrogenated over 10% Pd/C (0.5 g) at 50 psi for 72 h at ambient temperature. The reaction mixture is filtered and the filtrate is concentrated in vacuo. The resultant residue is dissolved in ethyl acetate and washed with saturated aqueous NaHCO3. The organic phase is dried over MgSO4, and concentrated in vacuo to afford the title compound as an amber oil, 0.85 g (89% yield), identified by NMR and mass spectral analyses.

Workup

  1. filtrationThe reaction mixture is filtered
  2. concentrationthe filtrate is concentrated in vacuo
  3. dissolutionThe resultant residue is dissolved in ethyl acetate
  4. washwashed with saturated aqueous NaHCO3
  5. dry with materialThe organic phase is dried over MgSO4
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e2da5b6fc92c4373bfb43f28abe30963
Source dataset
uspto-grants-2004_03
Patent number
US06706757B2

Reaction notes

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