Hydrochloric Acid → 4-Amino-2,3-difluoro-5-nitrobenzoic acid

HRID 216998Notes

Reaction equation

HRID 216998 reaction equation
[OH-].[NH4+:2].[F:3][C:4]1[C:12]([F:13])=[C:11](F)[C:10]([N+:15]([O-:17])=[O:16])=[CH:9][C:5]=1[C:6]([OH:8])=[O:7].Cl>O>[NH2:2][C:11]1[C:10]([N+:15]([O-:17])=[O:16])=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[C:4]([F:3])[C:12]=1[F:13]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14923Ammonium Hydroxide2×HCID 158712412,3,4-Trifluoro-5-nitrobenzoic acid

Product 1

HCID 162440884-Amino-2,3-difluoro-5-nitrobenzoic acidYield 95%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

Ammonium hydroxide solution (˜30% in water) (35 mL, 271 mmol) is added to a solution of 2,3,4-trifluoro-5-nitro-benzoic acid 2 (15 g, 67.8 mmol) in 30 mL water at 0° C. with stirring. Upon completion of ammonium hydroxide addition the reaction mixture is warmed to room temperature with stirring. After 2.5 hours, the reaction mixture is cooled to 0° C. and concentrated HCl is carefully added until pH of reaction mixture is near 0. The reaction mixture is diluted with water (30 mL) and extracted with diethyl ether (3×50 mL). The combined organic extracts are dried (MgSO4) and concentrated under reduced pressure to give 14 g (95%) of pure desired product: MS APCI (−) m/z 217 (M−1) detected.

Workup

  1. stirringwith stirring
  2. temperaturethe reaction mixture is cooled to 0° C.
  3. extractionextracted with diethyl ether (3×50 mL)
  4. dry with materialThe combined organic extracts are dried (MgSO4)
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-52d87c13ad0e4520a0e81c04d7243926
Source dataset
uspto-grants-2012_06
Patent number
US08193231B2

Reaction notes

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