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) 
(B) A. Thionyl chloride, B. 4-Chloropyridine C. Piperidine
(A) (B) 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