4-Nitrophenyl Acetate → HCID 21996530, compound

HRID 1978018Notes

Reaction equation

HRID 1978018 reaction equation
[NH2:1][CH2:2][CH2:3][CH:4]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([NH:14][CH:15]=O)[CH:12]=2)[CH2:7][CH2:6][CH2:5]1.[H-].[Al+3].[Li+].[H-].[H-].[H-].S([O-])([O-])(=O)=O.[Mg+2].[C:29](OC1C=CC([N+]([O-])=O)=CC=1)(=[O:31])[CH3:30]>C1COCC1.O.C(OCC)(=O)C>[C:29]([NH:1][CH2:2][CH2:3][CH:4]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([NH:14][CH3:15])[CH:12]=2)[CH2:7][CH2:6][CH2:5]1)(=[O:31])[CH3:30]

Participants

8

Reactant 4

HCID 132434-Nitrophenyl AcetateHCID 24083Sulfuric acid magnesium salt (1:1)HCID 21226445Aluminium lithium hydrideHCID 21996480HCID 21996480, compound

Product 1

HCID 21996530HCID 21996530, compoundYield 60.8%

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 1-(2-aminoethyl)-7-formylamino1,2,3,4-tetrahydronaphthalene (1.80 g, 8.25 mmol) in THF (20 ml) was added added, under ice-cooling, lithium aluminum hydride (0.63 g, 16.5 mmol). The mixture was heated for 4 hours under reflux under argon atmosphere. The reaction mixture was cooled with ice, to which was added water (0.9 ml), followed by further addition of ethyl acetate, anhydrous magnesium sulfate and celite, successively. The mixture was subjected to filtration, and the filtrate was concentrated under reduced pressure. The concentrate was dissolved in DMF (20 ml). To the solution was added 4-nitrophenyl acetate (1.33 g, 7.34 mmol), and the mixture was stirred for 20 minutes at room temperature. To the reaction mixture was added water, which was subjected to extraction with ethyl acetate. The extract solution was washed with brine, which was dried over anhydrous magnesium sulfate, followed by distilling off the solvent under reduced pressure. The residue was purified by means of a silica gel column chromatography (methanol/ethyl acetate, 97:3-96:5) to give 1.10 g (yield 54%) of the above-titled compound as an oily product.

Workup

  1. additionadded, under ice-
  2. temperaturecooling
  3. temperatureThe mixture was heated for 4 hours
  4. temperatureunder reflux under argon atmosphere
  5. temperatureThe reaction mixture was cooled with ice, to which
  6. filtrationThe mixture was subjected to filtration
  7. concentrationthe filtrate was concentrated under reduced pressure
  8. dissolutionThe concentrate was dissolved in DMF (20 ml)
  9. extractionwas subjected to extraction with ethyl acetate
  10. washThe extract solution was washed with brine, which
  11. dry with materialwas dried over anhydrous magnesium sulfate
  12. distillationby distilling off the solvent under reduced pressure
  13. customThe residue was purified by means of a silica gel column chromatography (methanol/ethyl acetate, 97:3-96:5)

Sources & evidence

ORD record
ord-c43bbe1e0cb04c65aa5725eacb714148
Source dataset
uspto-grants-2001_05
Patent number
US06235789B1

Reaction notes

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