4-Nitrophenol → HCID 86749976, compound

HRID 1900042Notes

Reaction equation

HRID 1900042 reaction equation
[CH:1]1[C:6]([N+:7]([O-:9])=[O:8])=[CH:5][CH:4]=[C:3]([OH:10])[CH:2]=1.C(=O)([O-])[O-].[K+].[K+].[CH3:17][O:18][C:19]1[C:28]([NH:29][C:30](=[O:41])[C:31]([CH3:40])([CH3:39])[CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37]Br)=[C:27]2[C:22]([C:23](=[O:42])[CH2:24][CH2:25][O:26]2)=[CH:21][CH:20]=1.[OH-].[Na+]>C(#N)C.O>[CH3:17][O:18][C:19]1[C:28]([NH:29][C:30](=[O:41])[C:31]([CH3:40])([CH3:39])[CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][O:10][C:3]2[CH:4]=[CH:5][C:6]([N+:7]([O-:9])=[O:8])=[CH:1][CH:2]=2)=[C:27]2[C:22]([C:23](=[O:42])[CH2:24][CH2:25][O:26]2)=[CH:21][CH:20]=1

Participants

7

Reactant 4

HCID 9804-NitrophenolHCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 86749977HCID 86749977, compound

Product 1

HCID 86749976HCID 86749976, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

49 mg of p-nitrophenol and 49 mg of potassium carbonate were added to a solution of 150 mg of N-(7-methoxy-4-chromanon-8-yl)-2,2-dimethyl-8-bromooctaneamide (252) in acetonitrile (5 ml), and the mixture was heated under reflux for 15 hr. 10 ml of water was added to the reaction mixture, and the mixture was made alkaline with 2N aqueous NaOH solution and extracted with ethyl acetate. The extract was washed with water and brine, dried over anhydrous magnesium sulfate, and the solvent was removed by distillation to give N-(7-methoxy-4-chromanon-8-yl)-2,2-dimethyl-8-p-nitrophenoxyoctaneamide. This product was dissolved in 10 ml of ethyl acetate, 50 mg of Pd-C (10%) was added thereto, and the mixture was stirred under hydrogen. The Pd catalyst was removed by filtration, and the solvent was removed to give N-(7-methoxy-4-chromanon-8-yl)-2,2-dimethyl-8-p-aminophenoxyoctaneamide. This product was dissolved in 10 ml of ethanol, 50 mg of PtO2 and 500 mg of 37% aqueous formaldehyde solution were added thereto, and the mixture was stirred under hydrogen at room temperature for 15 hr. The catalyst was removed by filtration, the filtrate was concentrated, and purified by silica gel column chromatography (ethyl acetate/hexane=1:1) to give 34 mg of the intended title compound. Ethanol in which a HCl gas had been dissolved was added thereto, and the solvent was removed by distillation to give a hydrochloride.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 15 hr
  3. extractionextracted with ethyl acetate
  4. washThe extract was washed with water and brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customthe solvent was removed by distillation

Sources & evidence

ORD record
ord-2eb57bded924450da3589e9e5fbad5f6
Source dataset
uspto-grants-1996_11
Patent number
US05574061

Reaction notes

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