Hydrochloric Acid → 2-Fluoro-4-(methylamino)-5-nitrobenzoic acid

HRID 1189629Notes

Reaction equation

HRID 1189629 reaction equation
[CH3:1][NH2:2].[F:3][C:4]1[CH:12]=[C:11](F)[C:10]([N+:14]([O-:16])=[O:15])=[CH:9][C:5]=1[C:6]([OH:8])=[O:7].Cl>O>[F:3][C:4]1[CH:12]=[C:11]([NH:2][CH3:1])[C:10]([N+:14]([O-:16])=[O:15])=[CH:9][C:5]=1[C:6]([OH:8])=[O:7]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 6329MethylamineHCID 27828222,4-Difluoro-5-nitrobenzoic acid

Product 1

HCID 595298342-Fluoro-4-(methylamino)-5-nitrobenzoic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Methylamine (13.5 mL, 40% in water) is added to an ice-cooled mixture of 2,4-difluoro-5-nitro-benzoic acid (10.0 g, 49 mmol) in water (100 mL) and it is stirred for 30 min at rt. The mixture is acidified with 6N aq HCl-solution and the precipitate is filtered, washed with water and dried at 60° C. The crude material is recrystallized from MeOH. The final product is slightly contaminated by its regioisomer 4-fluoro-2-methylamino-5-nitro-benzoic acid.

Workup

  1. temperaturecooled
  2. filtrationthe precipitate is filtered
  3. washwashed with water
  4. customdried at 60° C
  5. customThe crude material is recrystallized from MeOH

Sources & evidence

ORD record
ord-24b2373013454a2b8bab582d11a09a13
Source dataset
uspto-grants-2014_03
Patent number
US08674113B2

Reaction notes

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