4-(1H-pyrrol-1-ylmethyl)benzoic acid synthesis

6synthesis methods

Product Name:4-(1H-pyrrol-1-ylmethyl)benzoic acid
CAS Number:137025-10-6
Molecular formula:C12H11NO2
Molecular Weight:201.22

Benzoic acid, 4-(1H-pyrrol-1-ylmethyl)-, methyl ester

144693-29-8
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137025-10-6
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Yield:137025-10-6 94%

Reaction Conditions:

with water;sodium hydroxide at 20; for 24 h;

Steps:

4-(Pyrrol-1-ylmethyl)benzoic acid (2):

Methyl 4-(pyrrol-1-ylmethyl)benzoate (42) (196 mg, 0.91 mmol) was suspended in1 M NaOH (10.0 mL, 10.0 mmol) and stirred at room temperaturefor 24 h; 2.0 mL of dioxane were then added and stirred at roomtemperature for an additional 72 h. The pH was adjusted to 1 bythe addition of 1 M HCl and the white solid was filtered off toobtain compound 2 as white needles. Yield 94%; mp 152-155 C;1H NMR (400 MHz, DMSO-d6): d (ppm) 5.19 (s, CH2), 6.04 (s, 2H Ar-H), 6.82 (s, 2H, Ar-H), 7.23 (d, J = 7.6 Hz, 2H, Ar-H), 7.89 (d,J = 7.6Hz, 2H, Ar-H), 12.94 (br s, 1H, COOH); HR-MS (ESI): m/z calcdfor C12H10NO2 [MH] 200.0712, found: 200.0710; HPLCtR = 7.616 min (method 2) (Scheme 2).

References:

Berne, Sabina;Kova?i?, Lidija;Sova, Matej;Kra?evec, Nada;Gobec, Stanislav;Kri?aj, Igor;Komel, Radovan [Bioorganic and Medicinal Chemistry,2015,vol. 23,# 15,p. 4264 - 4276]

696-59-3 Synthesis