Pyridine → Methyl 4-anilinobenzoate

HRID 1777566Notes

Reaction equation

HRID 1777566 reaction equation
[NH2:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][CH:3]=1.[C:12]1(B(O)O)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.N1C=CC=CC=1>ClCCl.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[C:12]1([NH:1][C:2]2[CH:3]=[CH:4][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:10][CH:11]=2)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

6

Reactant 3

HCID 1049PyridineHCID 12082Methyl 4-aminobenzoateHCID 66827Phenylboronic Acid

Product 1

HCID 614877Methyl 4-anilinobenzoateYield 54.7%

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of methyl 4-aminobenzoate (0.200 g; 1.32 mmol), benzeneboronic acid (0.323 g; 2.65 mmol), copper acetate (0.481 g; 2.65 mmol) and pyridine (0.214 mL; 2.65 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 40% ethyl acetate in heptane) to yield 0.164 g (54%) of the title compound as a colourless solid.

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 40% ethyl acetate in heptane)

Sources & evidence

ORD record
ord-fce30a7094b448f0833f2cf2955bbc32
Source dataset
uspto-grants-2016_02
Patent number
US09266832B2

Reaction notes

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