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

HRID 1883390Notes

Reaction equation

HRID 1883390 reaction equation
[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.Cl[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.C(O)CCC>[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

Participants

7

Reactant 4

HCID 174Ethylene GlycolHCID 7504BenzylamineHCID 83742-Chlorobenzoic AcidHCID 62657Potassium Phosphate, Tribasic

Product 1

HCID 810952-((Phenylmethyl)amino)benzoic acidYield 48%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 2631-ButanolSolvent

Conditions

Temperature
100 °C

Procedure

Copper(I) iodide (19 mg, 0.10 mmol), K3PO4 (636 mg, 3.00 mmol), benzylamine (131 μL, 1.20 mmol), 2-chlorobenzoic acid (157 mg, 1.00 mmol), ethylene glycol (111 μL, 2.00 mmol) and 1-butanol (1.0 mL) were used and heated to 100° C. for 72 hours. The above workup procedure was followed and gave 2-(N-benzyl)aminobenzoic acid (109 mg, 48% isolated yield) as a light yellow solid.

Sources & evidence

ORD record
ord-4ed800f9d0ce42898a8000d2486b02c0
Source dataset
uspto-grants-2004_07
Patent number
US06759554B2

Reaction notes

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