Ammonia → Benzamide, 2-amino-3,5-dinitro-

HRID 437910Notes

Reaction equation

N.C12C(=CC=CC=1)[NH:7]C(=O)OC2=O.[N+:14]([C:17]1[CH:28]=[C:27]([N+:29]([O-:31])=[O:30])[CH:26]=[C:19]2[C:20](OC(=O)[NH:24][C:18]=12)=[O:21])([O-:16])=[O:15]>>[NH2:24][C:18]1[C:17]([N+:14]([O-:16])=[O:15])=[CH:28][C:27]([N+:29]([O-:31])=[O:30])=[CH:26][C:19]=1[C:20]([NH2:7])=[O:21]

Participants

Reactant 3

HCID 222Ammonia2×

HCID 8359Isatoic Anhydride

HCID 21176250HCID 21176250, compound

Product 1

HCID 198148Benzamide, 2-amino-3,5-dinitro-

Procedure

A process for the manufacture of 2-amino-3,5-dinitrobenzamide which comprises nitrating at -20° C. to 80° C. isatoic anhydride dissolved in an inert organic solvent with an acid mixture consisting of 85-100% strength nitric acid and oleum, said acid mixture containing 0.5 to 20 moles of sulfur trioxide per mole of nitric acid, to produce 3,5-dinitroisatoic anhydride, allowing the reaction mixture to separate into an organic phase and an acid phase containing the 3,5-dinitroisatoic anhydride, adding 20-30% strength aqueous ammonia to the resultant acid phase in an amount of 9 to 25 moles of ammonia per mol of isatoic anhydride, and reacting the ammonia and the acid phase to produce a high yield of 2-amino-3,5-dinitrobenzamide.

Workup

customto separate into an organic phase
additionan acid phase containing the 3,5-dinitroisatoic anhydride

Sources & evidence

ORD record: ord-2e55c5cd990d4c0c9759b087f342d772
Source dataset: uspto-grants-1977_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04032571

Reaction notes

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