Acetic Acid → HCID 19363369, compound

HRID 850485Notes

Reaction equation

HRID 850485 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][N:10]2[C:14](=[O:15])[C:13]3=[C:16]([N+:20]([O-])=O)[CH:17]=[CH:18][CH:19]=[C:12]3[C:11]2=[O:23])=[CH:4][CH:3]=1.C(O)C.C(O)(=O)C.[H][H]>[C].[Pd].CO>[NH2:20][C:16]1[CH:17]=[CH:18][CH:19]=[C:12]2[C:11]([N:10]([CH2:9][CH2:8][C:5]3[CH:6]=[CH:7][C:2]([OH:1])=[CH:3][CH:4]=3)[C:14](=[O:15])[C:13]=12)=[O:23]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 702EthanolHCID 19363431HCID 19363431, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 19363369HCID 19363369, compoundYield 24.1%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

10% Palladium-carbon catalyst (water content 50%, 200 mg) was added to a mixed solution of N-[2-(4-hydroxyphenyl)ethyl]-3-nitrophthalimide (1.67 g, 0.0053 mol, 1 eq) in methanol (20 ml)-ethanol (50 ml)-acetic acid (20 ml), and the mixture was stirred for 3 hours at room temperature in a stream of hydrogen. The reaction mixture was filtered through Celite, and the filtrate was concentrated under reduced pressure. The obtained residue was purified by column chromatography on silica gel (chloroform/methanol=50/1) to give 3-amino-N-[2-(4-hydroxyphenyl)ethyl]phthalimide (360 mg, 24.1%) as a colorless solid.

Workup

  1. filtrationThe reaction mixture was filtered through Celite
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe obtained residue was purified by column chromatography on silica gel (chloroform/methanol=50/1)

Sources & evidence

ORD record
ord-d32c4e1f187e4907ab13a9e1a1a58904
Source dataset
uspto-grants-2000_01
Patent number
US06017919

Reaction notes

Loading…