Aluminum(III) Chloride → Benzoic acid, 3-[(3-hydroxy-4-methoxyphenyl)(3-pyridinylmethyl)amino]-

HRID 750991Notes

Reaction equation

HRID 750991 reaction equation
C1([O:6][C:7]2[CH:8]=[C:9]([N:15]([CH2:25][C:26]3[CH:27]=[N:28][CH:29]=[CH:30][CH:31]=3)[C:16]3[CH:17]=[C:18]([CH:22]=[CH:23][CH:24]=3)[C:19]([OH:21])=[O:20])[CH:10]=[CH:11][C:12]=2[O:13][CH3:14])CCCC1.[Al+3].[Cl-].[Cl-].[Cl-]>C(Cl)Cl.O>[OH:6][C:7]1[CH:8]=[C:9]([N:15]([CH2:25][C:26]2[CH:27]=[N:28][CH:29]=[CH:30][CH:31]=2)[C:16]2[CH:17]=[C:18]([CH:22]=[CH:23][CH:24]=2)[C:19]([OH:21])=[O:20])[CH:10]=[CH:11][C:12]=1[O:13][CH3:14]

Participants

5

Reactant 2

HCID 6451240Aluminum(III) ChlorideHCID 9931830HCID 9931830, compound

Product 1

HCID 10360501Benzoic acid, 3-[(3-hydroxy-4-methoxyphenyl)(3-pyridinylmethyl)amino]-

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

N-(3-Cyclopentyloxy-4-methoxyphenyl)-N-(3-pyridylmethyl)-3-aminobenzoic acid (10.0 g, 23.9 mmol) was dissolved in DCM and 22.3 g (167 mmol) of AlCl3 was added. The dark brown solution stirred at room temperature overnight under N2. The reaction mixture was diluted with 100 mL of DCM and 100 mL of H2O and the pH of the aqueous phase adjusted to 5.5. The aqueous phase was extracted with 500 mL of EtOAc and the combined organic fractions were concentrated to dryness giving the desired compound.

Workup

  1. extractionThe aqueous phase was extracted with 500 mL of EtOAc
  2. concentrationthe combined organic fractions were concentrated to dryness

Sources & evidence

ORD record
ord-067bb7e58c264b518cb45da819251713
Source dataset
uspto-grants-2008_07
Patent number
US07405230B2

Reaction notes

Loading…