Hydrogen Peroxide → Imazaquin

HRID 638649

반응식

HRID 638649 반응식
[NH2:1][C:2]([CH3:8])([CH:5]([CH3:7])[CH3:6])[C:3]#[N:4].[N:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:12]=[C:11]2[C:19]([O:21][C:22](=O)[C:10]=12)=[O:20].N1C=CC(C)=CC=1.[OH-].[Na+].OO.S(=O)(=O)(O)[OH:36]>C1(C)C=CC=CC=1>[CH:5]([C:2]1([CH3:8])[C:3](=[O:36])[NH:4][C:22]([C:10]2[C:11]([C:19]([OH:21])=[O:20])=[CH:12][C:13]3[C:18](=[CH:17][CH:16]=[CH:15][CH:14]=3)[N:9]=2)=[N:1]1)([CH3:7])[CH3:6]

참가 물질

8

반응물 6

HCID 784Hydrogen PeroxideHCID 1118Sulfuric AcidHCID 79634-MethylpyridineHCID 14798Sodium Hydroxide3회HCID 943552-Amino-2,3-dimethylbutyronitrileHCID 4325463Furo[3,4-b]quinoline-1,3-dione

생성물 1

HCID 54739Imazaquin

시약·촉매·용매 1

HCID 1140Toluene용매2회

실험 절차

2-Amino-2,3-dimethylbutyronitrile (0.393 mol) is added over 40 minutes to a stirred solution of 2,3-quinolinedicarboxylic anhydride (0.376 mol) in 4-picoline (338 g, 3.63 mol) and toluene (52 g), while maintaining the temperature at 40° to 43° C. The reaction mixture is stirred at 40° to 43° C. for one hour. Aqueous sodium hydroxide (218 g, 25%, 1.36 mol) and then toluene 378 g) are added and the mixture stirred at 55° to 60° C. for approximately 15 minutes. The lower aqueous basic phase is separated off and the product extracted from organic phase with water. The aqueous phase is washed with toluene. A portion of the aqueous phase (25.8 g) is treated with 25% aqueous sodium hydroxide (10 g) and 3.7 equivalents of hydrogen peroxide at 65°-70° C. for one hour, then additional 50% aqueous sodium hydroxide (14.5 g) is added and the reaction mixture is allowed to stir for one hour at 65° to 70° C. The mixture is cooled to 25° to 30° C., and the pH of the mixture adjusted to 1.5 with concentrated sulfuric acid. The product 2-(4-isopropyl-4-methyl-5-oxo-2-imidazolin-2-yl)-3-quinolinecarboxylic acid (17.3 g) is isolated by filtration.

후처리

  1. temperaturewhile maintaining the temperature at 40° to 43° C
  2. stirringthe mixture stirred at 55° to 60° C. for approximately 15 minutes
  3. customThe lower aqueous basic phase is separated off
  4. extractionthe product extracted from organic phase with water
  5. washThe aqueous phase is washed with toluene
  6. stirringto stir for one hour at 65° to 70° C
  7. temperatureThe mixture is cooled to 25° to 30° C.

출처 및 근거

ORD 기록
ord-e92d3f44824e45658bc20188267f4e6f
출처 데이터셋
uspto-grants-1985_12
특허 번호
US04562257

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