Ethanol → 4-[(7-Oxo-7,8-dihydro[1,8]naphthyridin-4-yl)oxy]aniline

HRID 853319Notes

Reaction equation

HRID 853319 reaction equation
[N+:1]([C:4]1[CH:21]=[CH:20][C:7]([O:8][C:9]2[C:18]3[CH:17]=[CH:16][C:15](=[O:19])[NH:14][C:13]=3[N:12]=[CH:11][CH:10]=2)=[CH:6][CH:5]=1)([O-])=O.[Cl-].[NH4+].CN(C)C=O.C(O)C>[Fe].O>[O:19]=[C:15]1[NH:14][C:13]2[N:12]=[CH:11][CH:10]=[C:9]([O:8][C:7]3[CH:6]=[CH:5][C:4]([NH2:1])=[CH:21][CH:20]=3)[C:18]=2[CH:17]=[CH:16]1

Participants

7

Reactant 4

HCID 702EthanolHCID 6228DimethylformamideHCID 25517Ammonium ChlorideHCID 229368804-(4-Nitrophenoxy)-7-oxo-7,8-dihydro[1,8]naphthyridine

Product 1

HCID 589313574-[(7-Oxo-7,8-dihydro[1,8]naphthyridin-4-yl)oxy]aniline

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 962WaterSolvent

Procedure

4-(4-Nitrophenoxy)-7-oxo-7,8-dihydro[1,8]naphthyridine (156 mg), iron powder (300 mg), ammonium chloride (600 mg), dimethylformamide (2 ml), ethanol (1 ml) and water (1 ml) were stirred at 100° C. for 20 minutes. The mixture was filtered with celite, and then water and ethyl acetate were added for extraction. The organic layer was washed 4 times with aqueous ammonium chloride solution and then dried over magnesium sulfate. The drying agent was filtered off and the solvent was distilled off under reduced pressure to obtain 30 mg of the target substance as a light yellow solid.

Workup

  1. filtrationThe mixture was filtered with celite
  2. additionwater and ethyl acetate were added for extraction
  3. washThe organic layer was washed 4 times with aqueous ammonium chloride solution
  4. dry with materialdried over magnesium sulfate
  5. filtrationThe drying agent was filtered off
  6. distillationthe solvent was distilled off under reduced pressure
  7. customto obtain 30 mg of the target substance as a light yellow solid

Sources & evidence

ORD record
ord-31f6ab4ff14b4911930f692b7d155497
Source dataset
uspto-grants-2007_08
Patent number
US07253286B2

Reaction notes

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