Potassium Bromide → 5-Amino-2-(carboxymethyl)benzoic acid

HRID 909953Notes

Reaction equation

HRID 909953 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([C:14]([OH:16])=[O:15])[C:7](=[CH:12][CH:13]=1)[CH2:8][C:9]([OH:11])=[O:10])([O-])=O.[H][H].[K+].[Br-]>[OH-].[Na+].[Pd]>[NH2:1][C:4]1[CH:5]=[C:6]([C:14]([OH:16])=[O:15])[C:7](=[CH:12][CH:13]=1)[CH2:8][C:9]([OH:11])=[O:10]

Participants

6

Reactant 3

HCID 253877Potassium BromideHCID 123034522-(Carboxymethyl)-5-nitrobenzoic acidHCID 178418361HCID 178418361, compound

Product 1

HCID 125931265-Amino-2-(carboxymethyl)benzoic acidYield 81%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 14798Sodium HydroxideSolvent

Procedure

Compound 13 (15.75 g/0.07 mol) was then dissolved in 150 ml 1N NaOH, treated with 0.55 g of 5% Pd—C and placed in a 500 ml Parr bottle. The resultant mixture was hydrogenated at 47 psi for 3 hours or until the uptake of hydrogen ceased. The solution was suction filtered through Celite, washed with a minimum amount of DI water and then acidified with c. HCl to pH 4-5. The solution was stored in the refrigerator (scratch to induce crystallization) over night. The product crystallized and was isolated by suction filtration. A second and third crop can be obtained by allowing the filtrate to slowly concentrate at room temperature. The product formed: 11 g (81% yield). 1H NMR (d6-DMSO): δ 7.13 (s, 1H), 6.91 (d, J=8 Hz, 1H), 6.64 (d, J=8 Hz, 1H), 3.69 (s, 2H); IR (KBr): 3320-3640 (br), 1700 (s), 1550 (s) cm−1; EI-MS (m/z) 194.1 (M−); MS/MS 150; Anal. Calcd. for C9H9NO4.(H2O)0.25: C, 54.13; H, 4.80; N, 7.02%. Found: C, 54.09; H, 5.26; N, 7.01; Na, 0.29%.

Workup

  1. filtrationfiltered through Celite
  2. washwashed with a minimum amount of DI water
  3. customThe solution was stored in the refrigerator (scratch to induce crystallization) over night
  4. customThe product crystallized
  5. customwas isolated by suction filtration
  6. customA second and third crop can be obtained
  7. concentrationto slowly concentrate at room temperature
  8. customThe product formed

Sources & evidence

ORD record
ord-93b854090dcb4cd0a1d9064ea482f9ce
Source dataset
uspto-grants-2011_09
Patent number
US08021471B2

Reaction notes

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