Water → 6-bromo-4-(ethoxyamino)-1H-1,5-naphthyridin-2-one

HRID 1478544Notes

Reaction equation

HRID 1478544 reaction equation
[CH2:1]([O:3][NH2:4])[CH3:2].Cl.[Br:6][C:7]1[N:8]=[C:9]2[C:14](=[CH:15][CH:16]=1)[NH:13][C:12](=[O:17])[CH:11]=[C:10]2O.O.C(OCC)(=O)C>N1C=CC=CC=1>[Br:6][C:7]1[N:8]=[C:9]2[C:14](=[CH:15][CH:16]=1)[NH:13][C:12](=[O:17])[CH:11]=[C:10]2[NH:4][O:3][CH2:1][CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 76850O-ethylhydroxylamine hydrochlorideHCID 900429756-Bromo-4-hydroxy-1,5-naphthyridin-2(1H)-one

Product 1

HCID 900431286-bromo-4-(ethoxyamino)-1H-1,5-naphthyridin-2-one

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a suspension of EtONH2.HCl (1.05 g, 10.8 mmol) in pyridine (5 ml) was added 6-bromo-4-hydroxy-1H-1,5-naphthyridin-2-one (324 mg, 1.34 mmol) and stirring was continued for 17 h at 100° C. The mixture was allowed to cool to ambient temperature then water and ethyl acetate were added followed by separation of phases. The aqueous phase was extracted with ethyl acetate and the combined organic phases were dried over Na2SO4, filtered and concentrated in vacuo. Purification by flash chromatography eluting with ethyl acetate/MeOH, gradient, afforded 6-bromo-4-(ethoxyamino)-1H-1,5-naphthyridin-2-one.

Workup

  1. customfollowed by separation of phases
  2. extractionThe aqueous phase was extracted with ethyl acetate
  3. dry with materialthe combined organic phases were dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customPurification by flash chromatography
  7. washeluting with ethyl acetate/MeOH, gradient

Sources & evidence

ORD record
ord-694ea72fbd5f43c897a56e5802dd7760
Source dataset
uspto-grants-2016_08
Patent number
US09403845B2

Reaction notes

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