Nitrogen trioxide → 3-Cyanobenzoic acid

HRID 2304084Notes

Reaction equation

HRID 2304084 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][CH:11]=1)[C:6](N)=[O:7])#[N:2].N([N+]([O-])=O)=[O:13].CC1OC(OC2C(O)CC(OC3C(O)CC(OC4CC5CCC6C7(O)CC(OC(C)=O)C(C8COC(=O)C=8)C7(C)CCC6C5(C)CC4)OC3C)OC2C)CC(O)C1O>S(=O)(=O)(O)O>[C:1]([C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][CH:11]=1)[C:6]([OH:13])=[O:7])#[N:2]

Participants

5

Reactant 3

HCID 61526Nitrogen trioxideHCID 769743-CyanobenzamideHCID 9304916-(Acetyloxy)-3-{[2,6-dideoxyhexopyranosyl-(1->4)-2,6-dideoxyhexopyranosyl-(1->4)-2,6-dideoxyhexopyranosyl]oxy}-14-hydroxycard-20(22)-enolide

Product 1

HCID 158753-Cyanobenzoic acidYield 92%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

m-Cyanobenzamide (2.92 g) was added to a 70 wt. % aqueous sulfuric acid solution (100 ml), and the mixture was stirred under cooling with ice. The mixture was allowed to react while dinitrogen trioxide gas was introduced thereto at 336 N ml/hour for two hours. The precipitated crystals were collected through filtration, washed with water, and dried, to thereby obtain 2.68 g of m-cyanobenzoic acid (yield 92%, based on m-cyanobenzamide). The m-cyanobenzoic acid obtained had a purity of 99% or more.

Workup

  1. temperatureunder cooling with ice
  2. additionwas introduced
  3. filtrationThe precipitated crystals were collected through filtration
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-e266a14b7a464cd5baa627aba10816d2
Source dataset
uspto-grants-2002_08
Patent number
US06433211B1

Reaction notes

Loading…