Ammonia → 4-Carbamoyl-2-nitrobenzoic acid

HRID 1583454Notes

Reaction equation

HRID 1583454 reaction equation
[N+:1]([C:4]1[CH:13]=[C:12]([C:14]([O:16]C)=O)[CH:11]=[CH:10][C:5]=1[C:6]([O:8]C)=[O:7])([O-:3])=[O:2].[NH3:18]>>[N+:1]([C:4]1[CH:13]=[C:12]([C:14]([NH2:18])=[O:16])[CH:11]=[CH:10][C:5]=1[C:6]([OH:8])=[O:7])([O-:3])=[O:2]

Participants

3

Reactant 2

HCID 222AmmoniaHCID 21364Dimethyl nitroterephthalate

Product 1

HCID 135313384-Carbamoyl-2-nitrobenzoic acid

Procedure

This invention provides as new compositions of matter 2- and 3-nitroterephthalamic acids. This invention further provides a new process for the preparation of 2- and 3-nitroterephthalamic acids comprising the steps of reaction of a 1-4 carbon dialkyl nitroterephthalate with 20-51% by weight aqueous ammonia at 100°-200° C. under at least autogenous pressure for 1-6 hours at a dialkyl nitroterephthalate concentration of 10-40% by weight. Preferably 30-51% by weight aqueous ammonia is reacted at 150°-175° C. for 2-4 hours. For the preparation of 3-nitroterephthalamic acid it is preferred that the reaction be carried out using 20% by weight dimethyl nitroterephthalate and 25-51% by weight aqueous ammonia for 2-4 hours at 125°-175° C., most preferably at 150° C. 3-Nitroterephthalamic acid is isolated from the reaction mixture by cooling, removal of by-product nitroterephthalamide by filtration, adjustment of the pH of the filtrate to about 4 and removal of 3-nitroterephthalamic acid by filtration. For the preparation of 2-nitroterephthalamic acid, it is preferred that the reaction be carried out using about 10% by weight dimethyl nitroterephthalate and 25-51% by weight aqueous ammonia for 2-4 hours at 150°-200° C., most preferably at 175° C. 2-Nitroterephthalamic acid is isolated from the reaction mixture by cooling, removal of by-product nitroterephthalamide by filtration, adjusting the pH of the filtrate to about 4, removal of by-product 3-nitroterephthalamic acid by filtration, adjustment of the pH of the filtrate to about 2 and removing 2-nitroterephthalamic acid by filtration. The reaction may be summarized as follows: ##STR1##

Workup

  1. temperatureby cooling
  2. customremoval of by-product nitroterephthalamide
  3. filtrationby filtration, adjustment of the pH of the filtrate
  4. customto about 4 and removal of 3-nitroterephthalamic acid
  5. filtrationby filtration
  6. customFor the preparation of 2-nitroterephthalamic acid, it
  7. customfor 2-4 hours
  8. customat 150°-200° C.
  9. custommost preferably at 175° C

Sources & evidence

ORD record
ord-bf877ce42d0346b48c06aa21eec89e59
Source dataset
uspto-grants-1985_11
Patent number
US04551549

Reaction notes

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