4-(1H-PYRROL-1-YL)BENZOHYDRAZIDE synthesis

7synthesis methods

Product Name:4-(1H-PYRROL-1-YL)BENZOHYDRAZIDE
CAS Number:112575-84-5
Molecular formula:C11H11N3O
Molecular Weight:201.22

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112575-84-5
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Yield:112575-84-5 83%

Reaction Conditions:

with hydrazine in ethanol; for 3 h;Reflux;

Steps:

3.2.3. 4-(1H-Pyrrol-1-yl)benzoic acid hydrazide (17)

A solution of methyl 4-(1H-pyrrol-1-yl)benzoate (15) (1.2 g, 6 mmol) and anhydrous hydrazine (5 mL) in 96%ethanol (5 mL) was heated at reflux temperature for 3 h. The solvent was removed under reduced pressureand the residue was recrystallized from a small volume of 2-propanol to give colorless crystals (1 g, 83%), mp179-181 °C (lit.32 mp 180-182 °C; lit.36 mp 180-181 °C); 1 H NMR (DMSO-d6 , 400 MHz): 4.50 (br s, 2H,exchangeable with D), 6.29 (t, J = 2.0 Hz, 2H), 7.47 (t, J = 2.0 Hz, 2H), 7.68 (d, J = 8.8 Hz, 2H), 7.92 (d,J = 8.8 Hz, 2H), 9.81 (s, 1H, exchangeable with D); 13 C NMR (DMSO-d6 , 100 MHz): 111.1, 118.5, 119.0,128.6, 129.6, 141.8, 165.1. Anal. Calcd. for C11 H11 N3 O: C, 65.66; H, 5.51; N, 20.88. Found: C, 65.84; H,5.42; N, 21.02.

References:

Roman, Gheorghe;Bost?naru, Andra-Cristina;N?stas?, Valentin;Mare?, Mihai [Turkish Journal of Chemistry,2019,vol. 43,# 2,p. 531 - 546]