Anthranilic Acid → 2-(Nitroamino)benzoic acid

HRID 589481Notes

Reaction equation

HRID 589481 reaction equation
S(=O)(=O)(O)O.[NH2:6][C:7]1[CH:15]=[CH:14][CH:13]=[CH:12][C:8]=1[C:9]([OH:11])=[O:10].[N+:16]([O-])([OH:18])=[O:17].[NH4+].[OH-]>>[N+:16]([NH:6][C:7]1[CH:15]=[CH:14][CH:13]=[CH:12][C:8]=1[C:9]([OH:11])=[O:10])([O-:18])=[O:17]

Participants

5

Reactant 4

HCID 227Anthranilic AcidHCID 944Nitric AcidHCID 1118Sulfuric Acid2×HCID 14923Ammonium Hydroxide

Product 1

HCID 215441192-(Nitroamino)benzoic acidYield 75.4%

Procedure

To a solution of concentrated sulfuric acid (2 mL) was slowly added 2-aminobenzoic acid (CXXIV) (1.0 g, 7.24 mmol). A mixture of concentrated sulfuric acid (1.5 mL) and fuming nitric acid (1.5 mL) was then slowly added and the reaction was stirred at room temperature overnight. The reaction mixture was poured into crushed ice and treated with aqueous NH4OH until pH 3.0. The yellow-orange solid was washed with cold water and dried to produce 2-(nitroamino)benzoic acid (CXXV) as a yellow solid (1.0 g, 5.46 mmol, 75.4% yield). The crude product was used for the next step without further purification. ESIMS found for C7H6N2O4 m/z 183.9 (M+H).

Workup

  1. additionwas then slowly added
  2. additionThe reaction mixture was poured
  3. custominto crushed ice
  4. washThe yellow-orange solid was washed with cold water
  5. customdried

Sources & evidence

ORD record
ord-dd088a41f3fe49ae8514d2fc8c7df9e6
Source dataset
uspto-grants-2016_01
Patent number
US09233104B2

Reaction notes

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