Sodium Azide → N-(3-amino-4-chlorobenzyl)cyclopropanecarboxamide

HRID 59328Notes

Reaction equation

HRID 59328 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:8]([CH2:11][NH:12][C:13]([CH:15]2[CH2:17][CH2:16]2)=[O:14])=[CH:7][C:3]=1C(O)=O.[N-:18]=[N+]=[N-].[Na+]>OS(O)(=O)=O>[NH2:18][C:3]1[CH:7]=[C:8]([CH:9]=[CH:10][C:2]=1[Cl:1])[CH2:11][NH:12][C:13]([CH:15]1[CH2:17][CH2:16]1)=[O:14]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 715157952-Chloro-5-(cyclopropanecarboxamidomethyl)benzoic acid

Product 1

HCID 89035202N-(3-amino-4-chlorobenzyl)cyclopropanecarboxamideYield 70.3%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Conditions

Temperature
50 °C

Procedure

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)+.

Workup

  1. customThe reaction mass was quenched with ammonia and ice water
  2. customThe solid obtained
  3. filtrationwas filtered
  4. customsuck dried

Sources & evidence

ORD record
ord-7b3ad1a0ae89426d8ba7db709b01450e
Source dataset
uspto-grants-2016_09
Patent number
US09439890B2

Reaction notes

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