Réaction #87606

Équation de réaction

2-chloro-5-(cyclopropanecarboxamidomethyl)benzoic acid

NaN3

→

desired product

Rendement 70.3%

N-(3-amino-4-chlorobenzyl)cyclopropanecarboxamide

Rendement 70.3%

Solvants

H2SO4

Conditions de réaction

Traitement

1. 1
   AutreThe reaction mass was quenched with ammonia and ice water
2. 2
   AutreThe solid obtained
3. 3
   Filtrationwas filtered
4. 4
   Autresuck dried

Mode opératoire

To a solution of 2-chloro-5-(cyclopropanecarboxamidomethyl)benzoic acid (5.0 g, 19 mmol) in conc. H2SO4 (30 mL) was added NaN3 (1.4 g, 21 mmol) lotwise at 50° C. The reaction mixture was stirred at 50° C. for 18 h. The reaction mass was quenched with ammonia and ice water. The solid obtained was filtered and suck dried to afford 3.0 g of desired product. 1H NMR (300 MHz, DMSO d6): δ 0.66 (m, 4H), 1.56 (m, 1H), 4.12 (d, J=6.0 Hz, 2H), 5.27 (s, 2H), 6.41 (d, J=6.9 Hz, 1H), 6.61 (s, 1H), 7.10 (d, J=8.4 Hz, 1H), 8.48 (m, 1H); MS (m/z): 225.22 (M+H)+.

Source