Nitric Acid → 2,6-Dichloro-3-nitrobenzamide

HRID 1708932Notes

Reaction equation

HRID 1708932 reaction equation
[N+:1]([O-:4])(O)=[O:2].[Cl:5][C:6]1[CH:14]=[CH:13][CH:12]=[C:11]([Cl:15])[C:7]=1[C:8]([NH2:10])=[O:9].[OH-].[Na+]>OS(O)(=O)=O>[Cl:5][C:6]1[C:14]([N+:1]([O-:4])=[O:2])=[CH:13][CH:12]=[C:11]([Cl:15])[C:7]=1[C:8]([NH2:10])=[O:9]

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 14798Sodium HydroxideHCID 161832,6-Dichlorobenzamide

Product 1

HCID 133824032,6-Dichloro-3-nitrobenzamideYield 76.3%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent2×

Procedure

A solution of 12 g of fuming HNO3 (d=1.52) in 11 ml of concentrated H2SO4 is added at room temperature over a period of 30 minutes to a solution of 30.4 g of 2,6-dichlorobenzoic acid amide in 60 ml of concentrated H2SO4 (d=1.83). After stirring for 2 hours at room temperature, the reaction mixture is added to ice/H2O and adjusted to a pH of ~ 6 with 30% NaOH and the precipitating crystals are isolated by filtration, affording 28.7 g of 2,6-dichloro-3-nitrobenzoic acid amide (m.p. 163°-165° C.).

Workup

  1. customthe precipitating crystals are isolated by filtration

Sources & evidence

ORD record
ord-a6b1df03ceec4601b92e85128047cf3c
Source dataset
uspto-grants-1990_08
Patent number
US04946854

Reaction notes

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