Pyridine → Ethyl 3-(phenylamino)benzoate

HRID 1777570Notes

Reaction equation

HRID 1777570 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][CH:12]=1)[C:5]([O:7][CH2:8][CH3:9])=[O:6].[C:13]1(B(O)O)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.N1C=CC=CC=1>ClCCl.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[C:13]1([NH:1][C:2]2[CH:3]=[C:4]([CH:10]=[CH:11][CH:12]=2)[C:5]([O:7][CH2:8][CH3:9])=[O:6])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

6

Reactant 3

HCID 1049PyridineHCID 11400Ethyl 3-aminobenzoateHCID 66827Phenylboronic Acid

Product 1

HCID 69991060Ethyl 3-(phenylamino)benzoateYield 87.3%

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of ethyl 3-aminobenzoate (0.200 g; 1.21 mmol), benzeneboronic acid (0.295 g; 2.42 mmol), copper acetate (0.439 g; 2.42 mmol) and pyridine (0.196 mL; 2.42 mmol) in dichloromethane (8 mL) was stirred at room temperature overnight. The reaction mixture was filtered and concentrated in vacuo. The crude mixture was purified by flash chromatography on silica gel (eluent 5 to 35% ethyl acetate in heptane) to yield 0.255 g (87%) of the title compound as a yellow oil.

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationconcentrated in vacuo
  3. customThe crude mixture was purified by flash chromatography on silica gel (eluent 5 to 35% ethyl acetate in heptane)

Sources & evidence

ORD record
ord-5a125e103414474eb428fae3d090eb06
Source dataset
uspto-grants-2016_02
Patent number
US09266832B2

Reaction notes

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