4-Aminobenzoic Acid → 4-(1,3-dioxo-1,3,3a,4,7,7a-hexahydro-2H-4,7-methanoisoindol-2-yl)benzoic acid

HRID 1494621

반응식

HRID 1494621 반응식
[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][CH:3]=1.CC(N(C)C)=O.C1(C)C=CC=CC=1.[CH:24]12[CH2:30][CH:27]([CH:28]=[CH:29]1)[CH:26]1[C:31]([O:33][C:34](=O)[CH:25]21)=[O:32]>O>[O:32]=[C:31]1[CH:26]2[CH:25]([CH:24]3[CH2:30][CH:27]2[CH:28]=[CH:29]3)[C:34](=[O:33])[N:1]1[C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][CH:3]=1

참가 물질

6

반응물 4

HCID 9784-Aminobenzoic AcidHCID 1140TolueneHCID 13223826-62-0HCID 31374Dimethylacetamide

생성물 1

HCID 5486924-(1,3-dioxo-1,3,3a,4,7,7a-hexahydro-2H-4,7-methanoisoindol-2-yl)benzoic acid수율 94.5%

시약·촉매·용매 1

HCID 962Water용매

반응 조건

온도
165 °C

실험 절차

To 4-aminobenzoic acid (800 g, 5.83 mol) is added dimethylacetamide (2.5 l), toluene (1 l), and slowly with stirring bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic anhydride (956 g, 5.83 mol). After the addition the mixture is stirred for 1 hour, raised to 140° C. with removal of water (100 ml) azeotropically and then raised to 165° C. to remove the toluene. The mixture is cooled and the product precipitated into water (3 l). Filtration, washing with water, drying in an oven at 80° C. and recrystallisation from ethanol yields a white crystalline solid (1.56 kg, 94%). M.p.: 224°-228° C.

후처리

  1. additionAfter the addition the mixture
  2. customto remove the toluene
  3. temperatureThe mixture is cooled
  4. customthe product precipitated into water (3 l)
  5. filtrationFiltration
  6. washwashing with water
  7. customdrying in an oven at 80° C.
  8. customrecrystallisation from ethanol

출처 및 근거

ORD 기록
ord-d3a8efd0c8b9494ebc1bfc8142b95f30
출처 데이터셋
uspto-grants-1991_06
특허 번호
US05026871

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