Ethylene Glycol → 2-((Phenylmethyl)amino)benzoic acid

HRID 984628

Reaktionsgleichung

Reaktionsgleichung von HRID 984628
[O-]P([O-])([O-])=O.[K+].[K+].[K+].[CH2:9]([NH2:16])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.I[C:18]1[CH:26]=[CH:25][CH:24]=[CH:23][C:19]=1[C:20]([OH:22])=[O:21].C(O)CO>[Cu]I.CC(O)C>[CH2:9]([NH:16][C:18]1[CH:26]=[CH:25][CH:24]=[CH:23][C:19]=1[C:20]([OH:22])=[O:21])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Komponenten

7

Edukt 4

HCID 174Ethylene GlycolHCID 69412-Iodobenzoic acidHCID 7504BenzylamineHCID 62657Potassium Phosphate, Tribasic

Produkt 1

HCID 810952-((Phenylmethyl)amino)benzoic acidAusbeute 71 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 3776IsopropanolLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

Copper(I) iodide (10 mg, 0.05 mmol), K3PO4 (636 mg, 3.00 mmol), benzylamine (131 μL, 1.20 mmol), 2-iodobenzoic acid (248 mg, 1.00 mmol), ethylene glycol (111 μL, 2.00 mmol) and 2-propanol (1.0 mL) were used and heated at 80° C. for 18 hours. The above workup procedure was followed and gave 2-(N-benzyl)aminobenzoic acid (161 mg, 71% isolated yield) as a light yellow solid.

Quellen und Nachweise

ORD-Eintrag
ord-7c533e3b527c407584e755a2c5fd07d0
Quelldatensatz
uspto-grants-2005_03
Patentnummer
US06867298B2

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