Ethyl 3-(3-Aminophenyl)propionate → HCID 59654753, compound

HRID 2053263Notes

Reaction equation

HRID 2053263 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:12][C:11]([C:13]([OH:15])=O)=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.C([O:18][C:19](=[O:29])[CH2:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[C:24]([NH2:28])[CH:23]=1)C>CCOC(C)=O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[O:12][C:11]([C:13]([NH:28][C:24]3[CH:23]=[C:22]([CH2:21][CH2:20][C:19]([OH:29])=[O:18])[CH:27]=[CH:26][CH:25]=3)=[O:15])=[CH:10][CH:9]=2)=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 82314Ethyl 3-(3-Aminophenyl)propionateHCID 7389915-(4-Fluorophenyl)furan-2-carboxylic acid

Product 1

HCID 59654753HCID 59654753, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Carboxylic acid (76)(53 mg, 0.26 mmol) was coupled to aniline (124)(50 mg, 0.26 mmol) using Method C. During this reaction, hydrolysis occurred. The acid was re-dissolved in EtOAc (2 ml) and the organic layer was washed with 1M HCl (2×1 ml), dried (Na2SO4), filtered and the solvent removed in vacuo. The solid was recrystallised from a hot 10% EtOH in H2O mixture to give the title compound.

Workup

  1. customDuring this reaction, hydrolysis
  2. washthe organic layer was washed with 1M HCl (2×1 ml)
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. customthe solvent removed in vacuo
  6. customThe solid was recrystallised from a hot 10% EtOH in H2O mixture

Sources & evidence

ORD record
ord-e2441c5c10194961bdaf882066d4a56d
Source dataset
uspto-grants-2008_02
Patent number
US07326732B2

Reaction notes

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