Q11 · CSIR-NET Chemistry, December 2017
Paper: CSIR-NET December 2017 · Subject: Organic Chemistry · Chapter: Natural Products · Topic: Natural Products – General · Marks: 2 · Difficulty: Medium
Correct sequence of reagents (i)-(iii) required for the conversion of A to B is 
A. Thionyl chloride, B. 4-Chloropyridine, C. Piperidine
A. Thionyl chloride, B. 4-Chloropyridine, C. Piperidine(a)A, B and C
(b)A, C and B
(c)B, A and C
(d)C, A and B
Answer
Answer: C ✓ checked by 4AB · confidence medium
Explanation
First the amine of anthranilic acid displaces Cl from 4-chloropyridine (SNAr, B). Then SOCl₂ converts COOH into the acid chloride (A), and piperidine forms the amide (C). The order B, A, C avoids self-acylation (c).
Study loop for Natural Products