Water → Succinanilic acid, 3'-(dihydroxyboryl)-

HRID 54629

Reaction equation

HRID 54629 reaction equation
[C:1]1(=[O:7])[O:6][C:4](=[O:5])[CH2:3][CH2:2]1.[NH2:8][C:9]1[CH:10]=[C:11]([B:15]([OH:17])[OH:16])[CH:12]=[CH:13][CH:14]=1.O>N1C=CC=CC=1>[OH:16][B:15]([OH:17])[C:11]1[CH:10]=[C:9]([NH:8][C:1](=[O:7])[CH2:2][CH2:3][C:4]([OH:6])=[O:5])[CH:14]=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 962WaterHCID 7922Succinic anhydrideHCID 922693-Aminophenylboronic acid

Product 1

HCID 208171Succinanilic acid, 3'-(dihydroxyboryl)-Yield 72.6%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Succinic anhydride (5.00 grams, 0.05 mole) and (3-aminophenyl)boronic acid (7.75 grams, 0.05 mole) are dissolved in anhydrous pyridine (40 ml), and then allowed to stand overnight at room temperature. Water (20 ml) is added and the resulting solution allowed to stand for 1 hour. The product is then concentrated on a rotary evaporator at 85°-90° C. The resulting aqueous solution is Frozen in a dry-ice-acetone-slurry and lyophilized overnight. The lyophilized product is dissolved in water (50 ml) and acidified with concentrated HCl to approximately pH 1.0. The acidified solution is cooled in an ice bath for 1 hour, and the precipitate collected by filtration. The precipitate is recrystallized from boiling water (200 ml) and dried overnight in vacuo over NaOH pellets, to afford 8.60 grams (70% yield) of N-(3-dihydroxyborylphenyl)succinamic acid. Homogeneous by TLC (CHCl3 /CH3OH/CH3COOH; 60:35:5), Rf =0.5. Melting point 186°-188° C. The structure was confirmed by 300 MHz, 1H NMR spectrometry in d6 -DMSO.

Workup

  1. waitto stand for 1 hour
  2. concentrationThe product is then concentrated on a rotary evaporator at 85°-90° C
  3. temperatureThe resulting aqueous solution is Frozen in a dry-ice-acetone-slurry
  4. waitlyophilized overnight
  5. dissolutionThe lyophilized product is dissolved in water (50 ml)
  6. temperatureThe acidified solution is cooled in an ice bath for 1 hour
  7. filtrationthe precipitate collected by filtration
  8. customThe precipitate is recrystallized
  9. dry with materialdried overnight in vacuo over NaOH pellets

Sources & evidence

ORD record
ord-1391736cb1c34508aaf57410193dacbf
Source dataset
uspto-grants-1997_04
Patent number
US05623055

Linked notes

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