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

HRID 1489335

반응식

HRID 1489335 반응식
[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

참가 물질

5

반응물 3

HCID 962WaterHCID 7922Succinic anhydrideHCID 922693-Aminophenylboronic acid

생성물 1

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

시약·촉매·용매 1

HCID 1049Pyridine용매

실험 절차

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, 1 H NMR, spectrometry in d6 -DMSO.

후처리

  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

출처 및 근거

ORD 기록
ord-645231b343ed4e4cbe23b2bfb1dd4f3f
출처 데이터셋
uspto-grants-1997_10
특허 번호
US05677431

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