Ammonium Chloride → HCID 18969218, compound

HRID 398833Notes

Reaction equation

HRID 398833 reaction equation
[CH3:1][N:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][N:10]=2)[C:5]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([N+:18]([O-])=O)[CH:13]=2)=[CH:4][C:3]1=[O:21].[Cl-].[NH4+]>[Zn].CO>[NH2:18][C:14]1[CH:13]=[C:12]([C:5]2[C:6]3[C:11](=[N:10][CH:9]=[CH:8][CH:7]=3)[N:2]([CH3:1])[C:3](=[O:21])[CH:4]=2)[CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 2

HCID 25517Ammonium ChlorideHCID 18969195HCID 18969195, compound

Product 1

HCID 18969218HCID 18969218, compoundYield 82%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 887MethanolSolvent

Procedure

Zinc (4.4 g, 67 mmol) was added to a mixture of 1-methyl-4-(3-nitrophenyl)-1,8-naphthyridin-2(1H)-one (0.95 g, 3.4 mmol) obtained in Example 12, methanol (20 ml) and an aqueous solution (20 ml) of ammonium chloride (3.6 g, 67 mmol) under ice-cooling, and the mixture was stirred for 4 hours under ice-cooling and then for 3 hours at room temperature. After removing insoluble matter by filtration, the filtrate was concentrated under reduced pressure, water was added to the resulting residue, followed by extraction with chloroform. The organic layer was dried over anhydrous magnesium sulfate, magnesium sulfate was removed by filtration and then the resulting filtrate was concentrated under reduced pressure. Thereafter, the resulting residue was purified by silica gel column chromatography (toluene-ethyl acetate) to give 4-(3-aminophenyl)-1-methyl-1,8-naphthyridin-2(1H)one (693 mg, 82%).

Workup

  1. temperaturecooling
  2. waitfor 3 hours at room temperature
  3. customAfter removing insoluble matter
  4. filtrationby filtration
  5. concentrationthe filtrate was concentrated under reduced pressure, water
  6. additionwas added to the resulting residue
  7. extractionfollowed by extraction with chloroform
  8. dry with materialThe organic layer was dried over anhydrous magnesium sulfate, magnesium sulfate
  9. customwas removed by filtration
  10. concentrationthe resulting filtrate was concentrated under reduced pressure
  11. customThereafter, the resulting residue was purified by silica gel column chromatography (toluene-ethyl acetate)

Sources & evidence

ORD record
ord-445a1001e71842d78b16770651a84b54
Source dataset
uspto-grants-1998_10
Patent number
US05817670

Reaction notes

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