Ethyl 3-(3-Aminophenyl)propionate → HCID 59654708, compound

HRID 1444358Notes

Reaction equation

HRID 1444358 reaction equation
[Cl: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.[CH2:16]([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)[CH3:17]>CCOC(C)=O>[CH2:16]([O:18][C:19](=[O:29])[CH2:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[C:24]([NH:28][C:13]([C:11]2[O:12][C:8]([C:5]3[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=3)=[CH:9][CH:10]=2)=[O:15])[CH:23]=1)[CH3:17]

Participants

4

Reactant 2

HCID 82314Ethyl 3-(3-Aminophenyl)propionateHCID 7266935-(4-Chlorophenyl)-2-furoic acid

Product 1

HCID 59654708HCID 59654708, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Carboxylic acid (145) (58 mg, 0.26 mmol) was coupled to aniline (124) (50 mg, 0.26 mmol) using Method C. During this reaction, partial 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 to give a mixture of acid and ester, which was used without further purification.

Workup

  1. customDuring this reaction, partial 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. customto give
  7. customwas used without further purification

Sources & evidence

ORD record
ord-e8041c7a895b49b9806ac8de95ccc2df
Source dataset
uspto-grants-2010_02
Patent number
US07662839B2

Reaction notes

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