Tyramine → HCID 19363431, compound

HRID 850484Notes

Reaction equation

HRID 850484 reaction equation
[N+:1]([C:4]1[CH:14]=[CH:13][CH:12]=[C:6]2[C:7]([O:9][C:10](=[O:11])[C:5]=12)=O)([O-:3])=[O:2].[OH:15][C:16]1[CH:21]=[CH:20][C:19]([CH2:22][CH2:23][NH2:24])=[CH:18][CH:17]=1.C(OCC)(=O)C>C1(C)C=CC=CC=1>[OH:15][C:16]1[CH:21]=[CH:20][C:19]([CH2:22][CH2:23][N:24]2[C:10](=[O:11])[C:5]3=[C:4]([N+:1]([O-:3])=[O:2])[CH:14]=[CH:13][CH:12]=[C:6]3[C:7]2=[O:9])=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 5610TyramineHCID 8857Ethyl AcetateHCID 216313-Nitrophthalic anhydride

Product 1

HCID 19363431HCID 19363431, compoundYield 93.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

3-Nitrophthalic anhydride (1.93 g, 0.01 mol, 1 eq) and 2-(4-hydroxyphenyl)-ethylamine (2.06 g, 0.015 mol, 1.5 eq) were refluxed under heating in toluene (20 ml) for 3 hours. The reaction mi i t ure was cooled to room temperature, and ethyl acetate (100 ml) was added to this reaction mixture. The organic layer was washed twice with dil. aqueous hydrochloric acid solution (30 ml), further washed with saturated brine (100 ml), and dried over anhydrous sodium sulfate. After the drying agent was filtered off, the filtrate was concentrated under reduced pressure. The obtained residue was purified by column chromatography on silica gel (n-hexane/ethyl acetate=1/1) to give N-[2-(4-hydroxyphenyl)ethyl]-3-nitrophthalimide (2.92 g, 92.8%) as a colorless solid. This was further purified by recrystallization from methanol to give colorless crystals (1.9 g, 60.8%).

Workup

  1. washThe organic layer was washed twice with dil. aqueous hydrochloric acid solution (30 ml)
  2. washfurther washed with saturated brine (100 ml)
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationAfter the drying agent was filtered off
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customThe obtained residue was purified by column chromatography on silica gel (n-hexane/ethyl acetate=1/1)

Sources & evidence

ORD record
ord-4cf9b741d630484893d4b7afada701d7
Source dataset
uspto-grants-2000_01
Patent number
US06017919

Reaction notes

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