Hydrochloric Acid → 2-Amino-5-nitro-4-trifluoromethyl-benzoic acid

HRID 2069304Notes

Reaction equation

HRID 2069304 reaction equation
C[O:2][C:3](=[O:18])[C:4]1[CH:9]=[C:8]([N+:10]([O-:12])=[O:11])[C:7]([C:13]([F:16])([F:15])[F:14])=[CH:6][C:5]=1[NH2:17].[OH-].[Na+].Cl>CO>[NH2:17][C:5]1[CH:6]=[C:7]([C:13]([F:16])([F:15])[F:14])[C:8]([N+:10]([O-:12])=[O:11])=[CH:9][C:4]=1[C:3]([OH:18])=[O:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 11965778Methyl 2-amino-5-nitro-4-(trifluoromethyl)benzoate

Product 1

HCID 185367312-Amino-5-nitro-4-trifluoromethyl-benzoic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 490 mg (1.85 mmol) of 2-amino-5-nitro-4-trifluoromethyl-benzoic acid methyl ester in 5 ml methanol, 4.7 ml (9.27 mmol) of 2 M sodium hydroxide solution is added. The yellow solution is stirred at 60° C. for 12 hours. Subsequently hydrochloric acid (1M) is added to adjust to pH=2. The solvent volume is reduced by evaporation and is extracted with ethyl acetate. The organic layers are combined, dried and the solvent is evaporated to yield 2-amino-5-nitro-4-trifluoromethyl-benzoic acid. 1H-NMR; DMSO-d6 (400 MHz, ppm): 8.58 (s, 1H, aromatic); 8.10 (s(broad), 2H, NH2); 7.35 (s, 1H, aromatic).; LC-MS: 249 [M-H]- ; Agilent LC/MSD 1100 Series; LC-MS method: Column: SunFireCl8, 4.6*50 mm, 3.5 μm; negative MS; water/acetonitril 95:5 to 5:95 in 5 min, flow: 1.5 ml/min.

Workup

  1. customThe solvent volume is reduced by evaporation
  2. extractionis extracted with ethyl acetate
  3. customdried
  4. customthe solvent is evaporated

Sources & evidence

ORD record
ord-cbf92e5edf6742fdb3dee553bd6a516f
Source dataset
uspto-grants-2012_10
Patent number
US08299085B2

Reaction notes

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