Ammonia → 4-Carbamoyl-3-nitrobenzoic acid

HRID 906163Notes

Reaction equation

HRID 906163 reaction equation
C[O:2][C:3]([C:5]1[CH:13]=[CH:12][C:8]([C:9]([OH:11])=[O:10])=[CH:7][C:6]=1[N+:14]([O-:16])=[O:15])=O.[NH3:17]>>[NH2:17][C:3]([C:5]1[CH:13]=[CH:12][C:8]([C:9]([OH:11])=[O:10])=[CH:7][C:6]=1[N+:14]([O-:16])=[O:15])=[O:2]

Participants

3

Reactant 2

HCID 222AmmoniaHCID 98592Methyl hydrogen 2-nitroterephthalate

Product 1

HCID 70164254-Carbamoyl-3-nitrobenzoic acidYield 60%

Procedure

4-(Methoxycarbonyl)-3-nitrobenzoic acid (100 g, 0.44 mol) was taken into concentrated aqueous ammonia (37w %, 500 mL), and the resulting yellow solution was allowed to stir at room temperature over 12 hours. The solution was then reduced in volume to approximately 300 mL by rotary evaporation, and the solution was acidified to pH 2 by portion-wise addition of concentrated aqueous hydrochloric acid. The thick precipitate was collected by filtration and dried in vacuo to afford 4-(aminocarbonyl)-3-nitrobenzoic acid (51 g, 60% yield). 1H-NMR (d6-DMSO): 8.42 (d, 1H), 8.27 (dd, 1H), 8.26 (br s, 1H), 7.86 (br s, 1H), 7.76 (d, 1H).

Workup

  1. customThe solution was then reduced in volume to approximately 300 mL by rotary evaporation
  2. additionthe solution was acidified to pH 2 by portion-wise addition of concentrated aqueous hydrochloric acid
  3. filtrationThe thick precipitate was collected by filtration
  4. customdried in vacuo

Sources & evidence

ORD record
ord-0fc40cb155c6453596fa9449fb341c1b
Source dataset
uspto-grants-2011_09
Patent number
US08012956B2

Reaction notes

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