4-Anilino-3-nitrobenzoic acid → 3-Amino-4-phenylamino-benzoic acid

HRID 74146

Reaction equation

HRID 74146 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][C:12]=1[NH:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:7]([OH:9])=[O:8])([O-])=O.[H][H]>[Pd].O1CCCC1>[NH2:1][C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][C:12]=1[NH:13][C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)[C:7]([OH:9])=[O:8]

Participants

5

Reactant 2

HCID 38243664-Anilino-3-nitrobenzoic acidHCID 178418361HCID 178418361, compound2×

Product 1

HCID 7738213-Amino-4-phenylamino-benzoic acidYield 95.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A 3-neck flask was charged with 3-nitro-4-phenylaminobenzoic acid (see Synthesis Example 1-1) (1.67 g, 6.70 mmol), palladium/carbon (Pd:10%, 0.170 g), and tetrahydrofuran (34 mL), the atmosphere was replaced with hydrogen using three cycles of vacuum/hydrogen purge, and this was stirred at room temperature for 2.5 hours. After substituting in nitrogen, distilled water (20 mL) was added and this was stirred for 10 minutes, insoluble material was filtered off through a Celite layer (20 mm thickness), and this same layer was further washed with tetrahydrofuran (20 mL, 3 times). The filtrate and the wash solutions were combined, and the solvent was distilled off under reduced pressure. This was successively extracted with ethyl acetate (approx. 50 mL, 4 times), washed with distilled water (30 mL), and dried over anhydrous sodium sulfate, the solvent was distilled off under reduced pressure, and further drying under reduced pressure yielded the title compound (1.45 g, 95.3% yield) as a pale yellow solid.

Workup

  1. custompurge
  2. distillationdistilled water (20 mL)
  3. additionwas added
  4. stirringthis was stirred for 10 minutes
  5. filtrationinsoluble material was filtered off through a Celite layer (20 mm thickness)
  6. washthis same layer was further washed with tetrahydrofuran (20 mL, 3 times)
  7. distillationthe solvent was distilled off under reduced pressure
  8. extractionThis was successively extracted with ethyl acetate (approx. 50 mL, 4 times)
  9. washwashed with distilled water (30 mL)
  10. dry with materialdried over anhydrous sodium sulfate
  11. distillationthe solvent was distilled off under reduced pressure
  12. customfurther drying under reduced pressure

Sources & evidence

ORD record
ord-3f6cded859c546208933eab05023e6dc
Source dataset
uspto-grants-2014_09
Patent number
US08829035B2

Linked notes

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