5-Fluoro-2-nitrobenzoic acid → 2-Amino-5-fluorobenzoic acid

HRID 439320Notes

Reaction equation

HRID 439320 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([N+:11]([O-])=O)=[C:6]([CH:10]=1)[C:7]([OH:9])=[O:8]>C(O)C.[Pd]>[NH2:11][C:5]1[CH:4]=[CH:3][C:2]([F:1])=[CH:10][C:6]=1[C:7]([OH:9])=[O:8]

Participants

4

Reactant 1

HCID 27374205-Fluoro-2-nitrobenzoic acid

Product 1

HCID 1014122-Amino-5-fluorobenzoic acidYield 73%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a pressure flask capable of withstanding, 150 psi. was added 5-fluor-2-nitrobenzoic acid (2.0 g, 0.01 1 mol) dissolved in ethanol (40 mL) and 10% palladium on carbon (200 mg). The reaction was placed in a Parr apparatus and the flask flushed three times with hydrogen leaving an internal pressure of 65 psi. The reaction was continued for 16 hours while maintaining a pressure of 65 psi. The reaction was filtered through celite, washed with ethanol and the filtrate evaporated to dryness to give 2-amino-5-fluorobenzoic acid (1.22 g, 73%) as an off-white solid.: m.p. 183°-184°; 1H NMR (400 MHz, DMSO-d6) δ 6.75 (dd, 1H), 7.16 (dt, 1H), 7.36 (dd, 1H); 13C NMR (100 MHz, DMSO-d6) δ 109.3, 109.4, 115.4, 115.6, 117.8, 117.9, 121.5, 121.9, 148.3, 150.8, 153.8, 168.6, 168.7.

Workup

  1. customTo a pressure flask capable of withstanding
  2. customthe flask flushed three times with hydrogen leaving an internal pressure of 65 psi
  3. temperaturewhile maintaining a pressure of 65 psi
  4. filtrationThe reaction was filtered through celite
  5. washwashed with ethanol
  6. customthe filtrate evaporated to dryness

Sources & evidence

ORD record
ord-14fb6f32742c4ac0943ae4926109b974
Source dataset
uspto-grants-1996_05
Patent number
US05514676

Reaction notes

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