2-Methyl-2-(4-nitrophenoxymethyl)-2H-chromene → 2-(4-Aminophenoxymethyl)-2-methylchroman

HRID 2351514Notes

Reaction equation

HRID 2351514 reaction equation
[CH3:1][C:2]1([CH2:12][O:13][C:14]2[CH:19]=[CH:18][C:17]([N+:20]([O-])=O)=[CH:16][CH:15]=2)[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[O:3]1.[H][H]>CO.[Pd]>[NH2:20][C:17]1[CH:18]=[CH:19][C:14]([O:13][CH2:12][C:2]2([CH3:1])[CH2:11][CH2:10][C:9]3[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=3)[O:3]2)=[CH:15][CH:16]=1

Participants

5

Reactant 2

HCID 156711312-Methyl-2-(4-nitrophenoxymethyl)-2H-chromeneHCID 178418361HCID 178418361, compound

Product 1

HCID 156139132-(4-Aminophenoxymethyl)-2-methylchromanYield 70.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

780 mg of 2-methyl-2-(4-nitrophenoxymethyl)-2H-chromene (prepared as described in Preparation 3) were dissolved in 20 ml of methanol, and 160 mg of 10% w/w palladium-on-carbon were added to the solution. The solution was then hydrogenated at room temperature at a hydrogen pressure of about one atmosphere for about 10 hours. At the end of this time, the catalyst was filtered off, and the solvent was distilled off under reduced pressure. The residue was subjected to silica gel column chromatography eluted with a 2:1 by volume mixture of hexane and ethyl acetate, to afford 500 mg of the title compound as a pale yellow oily substance.

Workup

  1. filtrationAt the end of this time, the catalyst was filtered off
  2. distillationthe solvent was distilled off under reduced pressure
  3. washeluted with a 2:1 by volume mixture of hexane and ethyl acetate

Sources & evidence

ORD record
ord-02dcc00888a24e7585eda0836944cacf
Source dataset
uspto-grants-1989_10
Patent number
US04873255

Reaction notes

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